Asymmetric Aldol-Tishchenko Reaction of Sulfinimines

Vera M. Foley; Christina M. McSweeney; Kevin S. Eccles; Simon E. Lawrence; Gerard P. McGlacken

doi:10.1021/acs.orglett.5b02919

Asymmetric Aldol-Tishchenko Reaction of Sulfinimines

Vera M. Foley
, Christina M. McSweeney
, Kevin S. Eccles
, Simon E. Lawrence
, Gerard P. McGlacken

School of Chemistry

University College Cork

Research output: Contribution to journal › Article › peer-review

Abstract

Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol-Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a C=N in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1,3-amino alcohols in good diastereo- and enantioselectivity.

Original language	English
Pages (from-to)	5642-5645
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.5b02919
Publication status	Published - 20 Nov 2015

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title = "Asymmetric Aldol-Tishchenko Reaction of Sulfinimines",

abstract = "Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol-Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a C=N in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1,3-amino alcohols in good diastereo- and enantioselectivity.",

author = "Foley, \{Vera M.\} and McSweeney, \{Christina M.\} and Eccles, \{Kevin S.\} and Lawrence, \{Simon E.\} and McGlacken, \{Gerard P.\}",

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doi = "10.1021/acs.orglett.5b02919",

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T1 - Asymmetric Aldol-Tishchenko Reaction of Sulfinimines

AU - Foley, Vera M.

AU - McSweeney, Christina M.

AU - Eccles, Kevin S.

AU - Lawrence, Simon E.

AU - McGlacken, Gerard P.

PY - 2015/11/20

Y1 - 2015/11/20

N2 - Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol-Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a C=N in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1,3-amino alcohols in good diastereo- and enantioselectivity.

AB - Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol-Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a C=N in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1,3-amino alcohols in good diastereo- and enantioselectivity.

UR - https://www.scopus.com/pages/publications/84947939722

U2 - 10.1021/acs.orglett.5b02919

DO - 10.1021/acs.orglett.5b02919

M3 - Article

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SN - 1523-7060

VL - 17

SP - 5642

EP - 5645

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Asymmetric Aldol-Tishchenko Reaction of Sulfinimines

Abstract

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