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185 Davis chiral oxaziridine reagents Chiral N-sulfonyloxaziridines employed for asymmetric hydroxylation, etc. O N RSO 2 Ar e.g. S N O O O Cl Cl O N RSO 2 Ar R R 1 O M R R 1 O O M O N SO 2 R Ar R R 1 O M R R 1 O O N Ar RSO 2 R R 1 O O M Ar N SO 2 R Example 1 2 O N PhSO 2 Ph O N O O Ph O N O O Ph OH 1. NaHMDS, THF, 78 o C 85%, 90% de 2. THF, 78 o C 3. camphor sulfonic acid, THF

Davis Chiral Oxaziridine Reagents

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  • 185

    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).