Asymmetric synthesis of chiral sulfoxides and sulfinimines by using N-sulfinylsultam

Von Oppolzer, Wolfgang; Froelich, Olivier; Wiaux-Zamar, Chantal Marie Madeleine; Bernardinelli, Gérald Hugues

doi:10.1016/s0040-4039(97)00472-3

Scientific article

English

Asymmetric synthesis of chiral sulfoxides and sulfinimines by using N-sulfinylsultam

ContributorsVon Oppolzer, Wolfgang; Froelich, Olivier; Wiaux-Zamar, Chantal Marie Madeleine; Bernardinelli, Gérald Hugues

Published inTetrahedron letters, vol. 38, no. 16, p. 2825-2828

Publication date1997-04-21

First online date1998-03-26

Abstract

Bornane-10,2-sultam 1 is stereoselectively converted by DMAP-assisted sulfinylation to diastereomerically pure (2R)-N-[(R)-p-tolylsulfinyl]-bornane-10,2-sultam 2 in 77% yield. The crystalline sulfinylating agent 2 reacts with a variety of nucleophiles to afford sulfoxides 3 and sulfinimines 5 in excellent yields and enantioselectivities.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang et al. Asymmetric synthesis of chiral sulfoxides and sulfinimines by using N-sulfinylsultam. In: Tetrahedron letters, 1997, vol. 38, n° 16, p. 2825–2828. doi: 10.1016/s0040-4039(97)00472-3

Article (Published version)

Identifiers

PID : unige:155661
DOI : 10.1016/s0040-4039(97)00472-3

Commercial URLhttps://linkinghub.elsevier.com/retrieve/pii/S0040403997004723

ISSN of the journal0040-4039

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Asymmetric synthesis of chiral sulfoxides and sulfinimines by using N-sulfinylsultam

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