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Davis chiral oxaziridine reagents
Chiral N-sulfonyloxaziridines employed for asymmetric hydroxylation, etc.
ON
RSO2Ar
e.g.S
N
OO O
ClCl
ON
RSO2Ar
RR1
OM
RR1
O
O M
ON
SO2RAr
RR1
OM
RR1
O
O
N
Ar
RSO2
RR1
O
O M
Ar NSO2R
Example 12
ON
PhSO2Ph
ON
OO
PhON
OO
PhOH
1. NaHMDS, THF, 78 oC
85%, 90% de
2. THF, 78 oC
3. camphor sulfonic acid, THF
186
Example 25
NaHMDS, THF, 78 oC61%, 95% ee
Ph
O
SN
OO O
ClCl
Ph
O
OH
References
1 Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49,3241. Franklin A. Davis developed this methodology while teaching at Drexel Uni-versity, now he is at Temple University.
2 Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346. 3 Davis, F. A.; Billmers, J. M.; Gosciniak, D. J.; Towson, J. C.; Bach, R. D. J. Org.
Chem. 1986, 51, 4240. 4 Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703. (Review). 5 Davis, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55, 3715. 6 Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919934. (Review). 7 Davis, F. A.; Thimma Reddy, R.; Weismiller, M. C. J. Am. Chem. Soc. 1989, 111,
5964. 8 Davis, F. A.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1991, 56, 1143. 9 Davis, F. A.; Reddy, R. T.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428. 10 Tagami, K.; Nakazawa, N.; Sano, S.; Nagao, Y. Heterocycles 2000, 53, 771. 11 Takeda, K.; Sawada, Y.; Sumi, K. Org. Lett. 2002, 4, 1031. 12 Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E. Org. React. 2003, 62, 1356. (Re-
view).