title: Practical modifications and applications of the sharpless asymmetric aminohydroxylation in the one-pot preparation of chiral oxazolidin-2-ones.
abstract: [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.
authors.affiliation: Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. nancy.barta@pfizer.com
authors.forename: N S
authors.initials: NS
authors.lastname: Barta
authors.forename: D R
authors.initials: DR
authors.lastname: Sidler
authors.forename: K B
authors.initials: KB
authors.lastname: Somerville
authors.forename: S A
authors.initials: SA
authors.lastname: Weissman
authors.forename: R D
authors.initials: RD
authors.lastname: Larsen
authors.forename: P J
authors.initials: PJ
authors.lastname: Reider