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Supporting Information
Highly Enantioselective Synthesis of Syn-Aldols of Cyclohexanones
via Chiral Primary Amine Catalyzed Asymmetric Transfer Aldol
Reactions in Ionic Liquid
Pengxin Zhou, Sanzhong Luo*, Jin-Pei Cheng*
Department of Chemistry, State Key Laboratory of elemento-organic Chemistry, Nankai University,
Tianjin, 300071; China and Beijing National Laboratory for Molecule Sciences (BNLMS), CAS Key
Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of
Sciences, Beijing, 100190 China
2
NMR spectra for all the aldol products
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
1.
63
31
.6
49
1.
65
91
.6
83
1.
69
21
.7
02
1.
72
41
.7
35
1.
76
31
.7
76
1.
78
21
.7
91
1.
79
61
.8
05
1.
81
81
.8
26
1.
83
31
.8
73
1.
87
72
.0
37
2.
04
62
.0
56
2.
06
52
.0
77
2.
08
92
.0
99
2.
10
92
.3
46
2.
36
62
.3
90
2.
40
82
.4
19
2.
43
02
.4
63
2.
52
82
.5
36
2.
54
72
.5
55
2.
56
82
.5
77
2.
58
72
.5
96
2.
98
62
.9
97
3.
79
95
.3
12
5.
32
25
.3
31
6.
85
96
.8
88
7.
20
67
.2
34
7.
26
2
5.
31
1.
06
2.
09
1.
01
1.
00
3.
07
1.
03
2.
06
2.
01
200 180 160 140 120 100 80 60 40 20 ppm
24.89
26.18
27.99
42.69
55.25
57.28
70.39
76.61
77.03
77.46
113.56
126.92
133.61
158.60
214.91
O OH
OMe2a
O OH
OMe2a
3
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
16
1.
48
71
.5
18
1.
53
01
.5
41
1.
55
71
.5
72
1.
57
91
.5
85
1.
59
51
.6
04
1.
61
51
.6
26
1.
63
91
.6
55
1.
66
71
.6
83
1.
69
81
.7
09
1.
74
01
.7
52
1.
83
11
.8
69
1.
87
42
.0
70
2.
08
02
.0
90
2.
11
32
.1
23
2.
13
32
.3
73
2.
39
32
.4
18
2.
43
72
.4
43
2.
45
22
.4
58
2.
46
42
.4
73
2.
58
52
.5
90
2.
60
32
.6
09
2.
62
62
.6
32
3.
14
83
.1
59
5.
47
27
.2
48
7.
46
07
.4
89
8.
17
88
.2
07
4.
47
1.
10
1.
03
2.
07
1.
01
0.
99
1.
00
2.
00
1.
97
200 180 160 140 120 100 80 60 40 20 0 ppm
24.76
25.90
27.83
42.59
56.78
70.11
76.60
77.03
77.45
123.44
126.61
147.04
149.11
214.01
O OH
NO2
2b
O OH
NO2
2b
4
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
12
1.
51
41
.5
26
1.
62
11
.6
37
1.
64
81
.6
83
1.
69
41
.7
08
1.
72
11
.7
32
1.
75
11
.7
61
1.
80
01
.8
12
1.
85
01
.8
55
2.
03
62
.0
45
2.
05
42
.0
62
2.
08
82
.3
43
2.
36
32
.3
86
2.
38
82
.4
06
2.
41
52
.4
21
2.
42
62
.4
31
2.
43
62
.5
51
2.
55
72
.5
84
2.
61
12
.6
17
3.
01
13
.0
22
5.
36
85
.3
77
5.
38
67
.2
30
7.
24
57
.2
53
7.
25
87
.2
73
7.
29
57
.3
02
7.
31
37
.3
23
7.
32
67
.3
51
1.
16
3.
08
1.
03
1.
04
2.
08
1.
02
0.
98
1.
00
5.
10
200 180 160 140 120 100 80 60 40 20 ppm
24.88
26.01
27.95
42.68
57.20
70.61
76.61
77.04
77.46
125.76
126.97
128.16
141.50
214.77
O OH
2c
O OH
2c
5
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
1.
48
41
.5
25
1.
53
71
.5
67
1.
63
11
.6
46
1.
65
81
.6
73
1.
68
91
.7
00
1.
72
91
.7
42
1.
75
51
.7
65
1.
77
91
.7
89
1.
80
01
.8
11
1.
81
91
.8
51
1.
85
61
.8
62
1.
86
62
.0
42
2.
05
22
.0
61
2.
07
42
.0
85
2.
09
52
.1
05
2.
33
52
.4
11
2.
41
72
.4
23
2.
42
82
.4
33
2.
43
82
.4
67
2.
54
32
.5
49
2.
56
42
.5
70
2.
58
22
.5
89
2.
60
32
.6
09
2.
98
85
.3
47
7.
12
77
.1
54
7.
17
67
.2
04
7.
25
8
5.
94
1.
16
3.
11
2.
19
1.
08
1.
01
0.
02
0.
03
1.
00
4.
28
200 180 160 140 120 100 80 60 40 20 ppm
21.08
24.89
26.10
27.96
42.68
57.25
70.55
76.61
77.04
77.46
125.70
128.84
136.54
138.51
214.85
O OH
2dCH3
O OH
2dCH3
6
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.
00
11
.3
14
1.
49
81
.5
26
1.
53
91
.6
38
1.
64
91
.6
54
1.
66
51
.6
76
1.
68
01
.6
93
1.
70
71
.7
19
1.
74
91
.7
61
1.
78
91
.8
00
1.
81
31
.8
21
1.
83
21
.8
59
1.
86
61
.8
71
2.
04
82
.0
57
2.
06
72
.0
78
2.
09
02
.1
00
2.
35
12
.3
71
2.
39
52
.4
14
2.
42
92
.4
39
2.
56
32
.5
68
2.
58
22
.5
88
2.
60
42
.6
09
2.
62
12
.9
59
2.
96
65
.3
48
5.
35
75
.3
66
7.
21
37
.2
40
7.
25
97
.3
40
7.
36
8
9.
00
5.
14
1.
05
2.
09
1.
01
0.
97
0.
98
1.
95
1.
99
200 180 160 140 120 100 80 60 40 20 ppm
24.90
26.11
27.98
31.39
34.47
42.70
57.15
70.49
76.62
77.05
77.47
125.05
125.49
138.48
149.82
214.85
O OH
2e
O OH
2e
7
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.1
55
-0
.1
36
-0
.1
25
-0
.1
14
-0
.0
83
-0
.0
75
-0
.0
63
-0
.0
53
-0
.0
40
-0
.0
29
-0
.0
18
-0
.0
09
-0
.0
00
0.
01
00
.0
27
0.
04
00
.0
50
0.
08
20
.0
92
0.
13
50
.1
63
0.
20
40
.3
96
0.
40
50
.4
14
0.
43
80
.4
48
0.
45
70
.7
07
0.
72
70
.7
50
0.
76
80
.8
11
0.
82
10
.9
45
0.
95
20
.9
64
0.
97
10
.9
85
0.
99
31
.0
05
1.
01
11
.5
85
3.
79
35
.5
95
5.
80
45
.8
30
5.
85
65
.9
71
5.
99
66
.4
07
6.
43
46
.5
00
5.
46
1.
05
2.
06
1.
03
1.
00
0.
00
1.
00
-0
.0
0-
0.
00
1.
02
1.
02
0.
99
1.
01
200 180 160 140 120 100 80 60 40 20 ppm
23.22
24.39
26.32
41.06
55.24
68.38
75.13
75.55
75.98
119.37
120.54
127.62
130.47
142.42
146.80
212.52
O OH
2fNO2
O OH
2fNO2
8
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
00
1.
55
51
.5
97
1.
63
01
.6
39
1.
64
51
.6
56
1.
66
41
.6
72
1.
68
31
.6
95
1.
72
41
.7
34
1.
77
61
.8
17
1.
82
92
.0
71
2.
08
12
.3
79
2.
38
12
.3
98
2.
40
12
.4
23
2.
43
92
.4
51
2.
45
53
.1
86
3.
19
75
.6
63
6.
96
56
.9
69
6.
99
16
.9
96
7.
00
07
.0
04
7.
02
77
.0
31
7.
12
97
.1
50
7.
15
47
.1
75
7.
17
97
.2
08
7.
22
67
.2
33
7.
24
57
.2
51
7.
26
37
.5
02
7.
50
77
.5
27
7.
53
27
.5
52
5.
39
1.
04
2.
09
1.
00
0.
97
0.
99
1.
01
1.
03
1.
00
1.
00
200 180 160 140 120 100 80 60 40 20 ppm
24.85
26.23
27.96
42.64
55.01
65.30
65.32
76.60
77.03
77.45
114.72
115.01
123.94
123.99
128.20
128.26
128.33
128.44
157.32
214.77
O OH
2g
F
O OH
2g
F
9
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
1.614
1.674
1.682
1.698
1.708
1.727
1.739
1.824
1.832
1.872
1.877
2.066
2.075
2.091
2.101
2.110
2.117
2.308
2.329
2.353
2.374
2.397
2.418
2.434
2.439
2.464
2.469
2.478
2.523
2.531
2.557
2.583
2.591
3.054
3.065
5.342
5.351
5.360
7.222
7.250
7.262
7.293
7.321
4.39
1.03
1.03
2.07
1.02
0.99
1.00
4.23
200 180 160 140 120 100 80 60 40 20 ppm
24.84
25.97
27.91
42.64
57.03
70.13
76.59
77.01
77.43
127.17
128.31
132.68
140.00
214.52
O OH
2hCl
O OH
2hCl
10
8 7 6 5 4 3 2 1 0 ppm
1.
52
81
.5
34
1.
55
11
.5
74
1.
58
41
.5
89
1.
59
61
.6
13
1.
63
61
.6
49
1.
66
31
.6
75
1.
69
41
.7
03
1.
71
71
.8
13
1.
82
91
.8
46
1.
85
12
.0
45
2.
06
82
.0
77
2.
08
72
.0
98
2.
11
02
.1
21
2.
13
02
.2
82
2.
32
72
.3
46
2.
37
12
.3
89
2.
44
72
.4
93
2.
58
02
.6
04
2.
62
32
.6
42
4.
03
84
.0
52
5.
26
55
.2
78
5.
29
25
.3
05
7.
26
47
.2
72
7.
27
97
.3
01
7.
30
77
.3
48
7.
35
57
.4
82
7.
51
0
4.
58
1.
03
1.
12
1.
06
1.
03
1.
00
1.
00
0.
99
1.
24
0.
94
1.
00
200 180 160 140 120 100 80 60 40 20 ppm
24.90
27.75
30.37
42.71
57.51
70.13
76.60
77.02
77.45
127.62
128.91
129.26
133.52
133.80
137.83
215.06
O OH
2iCl
Cl
O OH
2iCl
Cl
11
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
00
1.
45
21
.4
66
1.
47
71
.4
94
1.
50
71
.5
19
1.
53
81
.5
48
1.
56
01
.5
77
1.
61
91
.6
45
1.
66
01
.6
73
1.
69
01
.7
03
1.
71
71
.7
28
1.
75
31
.7
64
1.
79
91
.8
39
2.
05
72
.0
64
2.
07
42
.0
99
2.
10
92
.3
40
2.
38
42
.4
04
2.
42
82
.4
48
2.
46
12
.5
06
2.
67
72
.7
06
2.
73
33
.1
48
3.
15
95
.5
66
7.
25
67
.3
44
7.
37
37
.3
76
7.
42
77
.4
50
7.
46
37
.4
75
7.
49
87
.7
98
7.
80
77
.8
25
1.
26
4.
25
1.
03
2.
06
1.
00
0.
99
1.
00
1.
02
1.
99
3.
99
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
24.88
26.07
27.98
42.72
57.10
70.72
76.60
77.02
77.44
123.89
124.53
125.66
126.09
127.63
127.83
127.95
132.62
133.25
138.86
214.87
O OH
2j
O OH
2j
12
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
05
1.
51
51
.5
22
1.
53
41
.5
46
1.
55
51
.5
75
1.
58
41
.6
24
1.
63
51
.6
41
1.
65
11
.6
64
1.
68
41
.6
94
1.
70
41
.7
18
1.
72
51
.7
47
1.
75
71
.8
04
1.
81
51
.8
25
1.
84
71
.8
57
2.
04
02
.0
62
2.
07
92
.3
54
2.
37
32
.3
93
2.
40
92
.6
76
2.
68
32
.7
09
2.
73
62
.7
43
3.
05
93
.0
71
3.
76
43
.7
95
5.
53
05
.5
40
5.
55
06
.4
18
6.
42
66
.4
77
6.
48
56
.5
05
6.
51
37
.2
60
7.
31
87
.3
46
4.
32
1.
04
1.
07
2.
05
1.
01
0.
99
3.
02
3.
02
1.
00
1.
00
1.
02
1.
00
200 180 160 140 120 100 80 60 40 20 ppm
24.89
26.45
28.07
42.73
54.57
55.24
55.34
65.94
76.62
77.04
77.47
98.20
103.81
121.96
127.98
156.36
159.76
215.51
O OH
2k
OMe
OMe
O OH
2k
OMe
OMe
13
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
1.
63
41
.6
50
1.
66
71
.6
78
1.
69
41
.7
09
1.
72
01
.7
67
1.
77
61
.7
86
1.
83
01
.8
75
1.
87
92
.0
53
2.
06
22
.0
86
2.
09
62
.2
97
2.
31
82
.3
42
2.
36
22
.3
85
2.
40
32
.4
13
2.
44
82
.4
58
2.
50
72
.5
17
2.
52
62
.5
48
2.
55
82
.9
93
3.
00
2
5.
27
6
5.
93
2
6.
74
96
.7
56
6.
81
5
7.
25
77
.2
63
5.
24
1.
06
3.
13
0.
97
1.
00
2.
03
1.
98
1.
02
200 180 160 140 120 100 80 60 40 20 ppm
24.87
26.15
27.97
42.67
57.32
70.50
76.61
77.03
77.45
100.91
106.59
107.98
118.84
135.54
146.42
147.55
214.80
O OH
2lO
O
O OH
2lO
O
14
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
00
1.
56
01
.6
65
1.
67
01
.6
81
1.
70
81
.7
35
1.
74
61
.7
75
1.
78
71
.7
95
1.
81
01
.8
15
1.
82
51
.8
38
1.
84
92
.0
76
2.
08
52
.3
76
2.
39
62
.3
98
2.
42
12
.4
37
2.
44
02
.4
46
2.
45
12
.4
57
2.
46
22
.4
67
2.
63
73
.0
22
3.
03
35
.4
23
5.
43
25
.4
41
7.
25
67
.3
08
7.
33
27
.3
39
7.
36
17
.3
88
7.
40
67
.4
26
7.
43
17
.4
49
7.
45
57
.5
57
7.
56
37
.5
78
7.
58
47
.5
94
7.
60
17
.6
06
4.
33
1.
02
2.
04
1.
01
0.
99
1.
00
5.
04
4.
01
200 180 160 140 120 100 80 60 40 20 ppm
24
.9
22
6.
12
27
.9
6
42
.7
0
57
.1
8
70
.5
27
6.
58
77
.0
07
7.
43
12
6.
21
12
6.
90
12
7.
04
12
7.
20
12
8.
74
13
9.
91
14
0.
58
14
0.
89
21
4.
72
O OH
Ph2m
O OH
Ph2m
15
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
00
1.
53
21
.6
82
1.
69
51
.7
13
1.
72
51
.7
38
1.
75
31
.7
81
1.
79
31
.8
35
1.
85
61
.8
67
1.
90
12
.0
29
2.
04
02
.3
30
2.
35
02
.3
74
2.
45
22
.4
63
2.
47
42
.5
09
2.
76
32
.7
81
2.
80
22
.8
18
2.
83
22
.8
53
2.
97
82
.9
90
3.
00
73
.0
30
3.
04
63
.7
62
3.
77
93
.7
90
3.
80
64
.4
49
4.
46
25
.6
66
5.
67
65
.6
87
7.
15
77
.1
80
7.
20
57
.2
32
7.
24
87
.2
53
7.
26
87
.2
74
7.
36
87
.3
93
1.
08
4.
31
1.
06
1.
05
1.
05
3.
09
2.
07
4.
10
1.
01
1.
00
3.
27
1.
02
200 180 160 140 120 100 80 60 40 20 ppm
24.76
26.38
27.61
42.53
53.63
56.31
67.53
68.40
76.62
77.04
77.47
122.04
125.55
127.68
127.90
137.50
149.60
213.82
O OH2n N
O
O OH2n N
O
16
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
1.
43
11
.4
62
1.
47
41
.6
22
1.
63
31
.6
54
1.
66
01
.6
92
1.
70
31
.7
43
1.
86
41
.8
77
1.
89
21
.8
97
1.
90
32
.0
61
2.
07
92
.0
90
2.
11
02
.1
17
2.
12
62
.1
36
2.
32
82
.3
48
2.
37
02
.4
23
2.
45
12
.4
73
2.
49
32
.5
15
3.
67
83
.6
89
4.
40
14
.4
12
4.
42
64
.4
37
4.
45
14
.4
62
6.
14
86
.1
72
6.
20
16
.2
25
6.
57
76
.6
30
7.
22
97
.2
38
7.
25
37
.2
57
7.
28
17
.3
06
7.
32
97
.3
69
7.
39
4
1.
05
2.
22
1.
07
2.
06
3.
07
0.
99
1.
00
0.
99
0.
99
5.
13
200 180 160 140 120 100 80 60 40 20 ppm
24.86
27.38
27.62
42.61
55.60
70.62
76.61
77.04
77.46
126.42
127.56
128.55
129.01
130.86
136.78
214.33
O OH
2oPh
O OH
2oPh
17
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
22
1.
59
22
.4
33
2.
48
02
.6
45
2.
66
92
.6
84
2.
70
72
.7
31
2.
75
52
.8
83
2.
89
22
.9
05
2.
91
52
.9
25
2.
93
82
.9
48
2.
96
62
.9
79
3.
65
63
.6
66
3.
69
43
.7
04
3.
73
33
.7
46
3.
78
23
.8
16
3.
83
83
.8
53
3.
87
64
.1
94
4.
21
84
.2
24
4.
23
14
.2
55
4.
95
24
.9
62
4.
97
84
.9
90
5.
52
4
7.
24
47
.4
79
7.
50
8
8.
18
88
.2
16
1.
06
1.
09
2.
06
3.
23
1.
06
1.
00
2.
09
2.
04
200 180 160 140 120 100 80 60 40 20 ppm
43.07
57.20
67.53
68.30
68.87
76.55
76.97
77.39
123.68
126.33
148.03
208.24
O
O OH
NO2
2p
O
O OH
NO2
2p
18
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
-0
.0
19
2.
48
82
.4
97
2.
51
92
.5
27
2.
76
92
.7
85
2.
80
12
.8
17
2.
87
32
.8
87
2.
89
62
.9
02
2.
91
82
.9
30
2.
93
92
.9
54
2.
97
42
.9
85
2.
99
93
.0
18
3.
03
23
.0
50
3.
07
13
.0
89
3.
10
1
5.
50
5
7.
24
77
.4
91
7.
52
0
8.
19
68
.2
25
0.
99
2.
12
4.
08
1.
11
1.
00
2.
06
2.
00
200 180 160 140 120 100 80 60 40 20 ppm
29
.4
63
0.
80
45
.0
4
59
.2
3
70
.2
47
6.
60
77
.0
27
7.
44
12
3.
69
12
6.
69
14
7.
32
14
8.
14
21
0.
93
S
O OH
NO2
2q
S
O OH
NO2
2q
19
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.
00
01
.6
51
1.
69
21
.7
02
1.
71
21
.9
71
1.
98
81
.9
93
2.
00
52
.0
15
2.
03
22
.0
78
2.
12
22
.4
17
2.
41
92
.4
53
2.
46
42
.4
69
2.
48
02
.7
08
2.
73
22
.9
41
2.
94
62
.9
49
2.
96
22
.9
74
3.
83
83
.8
45
3.
85
23
.8
67
3.
86
93
.8
81
3.
88
93
.8
96
3.
91
33
.9
18
3.
92
33
.9
29
3.
93
63
.9
40
3.
94
65
.4
17
5.
42
75
.4
36
7.
24
37
.2
62
7.
26
77
.2
72
7.
29
67
.3
15
7.
32
27
.3
35
7.
33
8
1.
36
3.
16
1.
06
1.
07
2.
04
4.
24
1.
00
5.
33
200 180 160 140 120 100 80 60 40 20 ppm
32.91
34.37
38.59
53.19
64.46
64.71
70.13
76.61
77.03
77.45
107.59
125.64
127.04
128.25
141.06
212.67
O OH
2r
O O
O OH
2r
O O
20
HPLC traces
O OH
OMe2a
O OH
OMe2a
21
O OH
NO2
2b
O OH
NO2
2b
22
O OH
2c
O OH
2c
23
O OH
2dCH3
O OH
2dCH3
24
O OH
2e
O OH
2e
25
O OH
2fNO2
O OH
2fNO2
26
O OH
2g
F
O OH
2g
F
27
O OH
2hCl
O OH
2hCl
28
O OH
2iCl
Cl
O OH
2iCl
Cl
29
O OH
2j
O OH
2j
30
O OH
2k
OMe
OMe
O OH
2k
OMe
OMe
31
O OH
2lO
O
O OH
2lO
O
32
O OH
Ph2m
O OH
Ph2m
33
O OH2n N
O
O OH2n N
O
34
O OH
2oPh
O OH
2oPh
35
O
O OH
NO2
2p
O
O OH
NO2
2p
36
S
O OH
NO2
2q
S
O OH
NO2
2q
37
O OH
2r
O O
O OH
2r
O O
38
Representative 1H NMR of crude reaction mixture for the transfer aldol of rac-2b
rac-2b
[BMIM]BF4, 50 oC
O OH O OH
(S, S)-2b
NO2NO2
1 (20 mol%)
acetone
O OH
NO2
+
10 9 8 7 6 5 4 3 2 1 0 ppm
4.
77
74
.8
15
4.
84
45
.1
77
5.
19
25
.2
02
5.
21
75
.4
13
7.
15
97
.1
94
7.
40
67
.4
34
7.
45
97
.4
87
8.
12
38
.1
29
8.
15
2
0.
03
1.
30
1.
00
0.
01
O OH
(S, S)-2b
NO2
O OH
NO2
