Enantioselective organocatalytic aldehyde-aldehyde cross-aldol couplings. The broad utility of α-thioacetal aldehydes

R. Ian Storer; David W.C. MacMillan

doi:10.1016/j.tet.2004.04.089

Enantioselective organocatalytic aldehyde-aldehyde cross-aldol couplings. The broad utility of α-thioacetal aldehydes

R. Ian Storer, David W.C. MacMillan

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

96 Scopus citations

Abstract

An asymmetric proline catalyzed aldol reaction with α-thioacetal aldehydes has been developed. Thioacetal bearing aldehydes readily participate as electrophilic cross-aldol partners with a broad range of aldehyde and ketone donors. High levels of reaction efficiency as well as diastereo- and enantiocontrol are observed in the production of anti-aldol adducts.

Original language	English (US)
Pages (from-to)	7705-7714
Number of pages	10
Journal	Tetrahedron
Volume	60
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2004.04.089
State	Published - Aug 23 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Aldol
Catalysis
Diastereoselection
Enantioselective
Organocatalysis
Proline

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10.1016/j.tet.2004.04.089

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title = "Enantioselective organocatalytic aldehyde-aldehyde cross-aldol couplings. The broad utility of α-thioacetal aldehydes",

abstract = "An asymmetric proline catalyzed aldol reaction with α-thioacetal aldehydes has been developed. Thioacetal bearing aldehydes readily participate as electrophilic cross-aldol partners with a broad range of aldehyde and ketone donors. High levels of reaction efficiency as well as diastereo- and enantiocontrol are observed in the production of anti-aldol adducts.",

keywords = "Aldol, Catalysis, Diastereoselection, Enantioselective, Organocatalysis, Proline",

author = "{Ian Storer}, R. and MacMillan, {David W.C.}",

note = "Funding Information: Financial support was provided by kind gifts from Bristol-Myers Squibb, Eli Lilly, and Merck Research Laboratories. D.W.C.M is grateful for support from the Sloan Foundation and Research Corporation. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

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language = "English (US)",

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AU - Ian Storer, R.

AU - MacMillan, David W.C.

N1 - Funding Information: Financial support was provided by kind gifts from Bristol-Myers Squibb, Eli Lilly, and Merck Research Laboratories. D.W.C.M is grateful for support from the Sloan Foundation and Research Corporation. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2004/8/23

Y1 - 2004/8/23

N2 - An asymmetric proline catalyzed aldol reaction with α-thioacetal aldehydes has been developed. Thioacetal bearing aldehydes readily participate as electrophilic cross-aldol partners with a broad range of aldehyde and ketone donors. High levels of reaction efficiency as well as diastereo- and enantiocontrol are observed in the production of anti-aldol adducts.

AB - An asymmetric proline catalyzed aldol reaction with α-thioacetal aldehydes has been developed. Thioacetal bearing aldehydes readily participate as electrophilic cross-aldol partners with a broad range of aldehyde and ketone donors. High levels of reaction efficiency as well as diastereo- and enantiocontrol are observed in the production of anti-aldol adducts.

KW - Aldol

KW - Catalysis

KW - Diastereoselection

KW - Enantioselective

KW - Organocatalysis

KW - Proline

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DO - 10.1016/j.tet.2004.04.089

M3 - Article

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VL - 60

SP - 7705

EP - 7714

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Enantioselective organocatalytic aldehyde-aldehyde cross-aldol couplings. The broad utility of α-thioacetal aldehydes

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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