Practical modifications and applications of the sharpless asymmetric aminohydroxylation in the one-pot preparation of chiral oxazolidin-2-ones.
[reaction: see text] Chiral oxazolidin-2-ones are synthetically valuable as chiral auxiliaries, and many have pharmaceutically interesting biological activity. This communication focuses on a convenient, practical one-pot preparation of chiral 4,5-disubstituted oxazolidan-2-ones in good yield with high enantioselectivities, using a modified Sharpless asymmetric aminohydroxylation of beta-substituted styrene derivatives followed by base-mediated ring closure. This procedure has been demonstrated on both small and large scale, utilizing 1, 3-dichloro-5,5-dimethyl hydantoin as an easily handled, commercially available substitute for tert-butyl hypochlorite.
Barta
N S
NS
Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. nancy.barta@pfizer.com
Sidler
D R
DR
Somerville
K B
KB
Weissman
S A
SA
Larsen
R D
RD
Reider
P J
PJ