Direct, pyrrolidine sulfonamide promoted enantioselective aldol reactions of α,α-dialkyl aldehydes: Synthesis of quaternary carbon-containing β-hydroxy carbonyl compounds

Wei Wang; Hao Li; Jian Wang

doi:10.1016/j.tetlet.2005.05.067

Direct, pyrrolidine sulfonamide promoted enantioselective aldol reactions of α,α-dialkyl aldehydes: Synthesis of quaternary carbon-containing β-hydroxy carbonyl compounds

Wei Wang, Hao Li, Jian Wang

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

86 Scopus citations

Abstract

A procedure has been developed for direct, asymmetric aldol reactions of α,α-dialkyl aldehydes with aromatic aldehydes, which produces quaternary carbon-containing β-hydroxy carbonyl compounds. The processes, promoted by the organocatalyst (S) pyrrolidine sulfonamide, take place in high yields with exceptionally high levels of enantioselectivities.

Original language	English (US)
Pages (from-to)	5077-5079
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2005.05.067
State	Published - Jul 25 2005
Externally published	Yes

Keywords

Aldehyde
Aldol reaction
Asymmetric catalysis
Organocatalyst
Pyrrolidine sulfonamide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.05.067

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title = "Direct, pyrrolidine sulfonamide promoted enantioselective aldol reactions of α,α-dialkyl aldehydes: Synthesis of quaternary carbon-containing β-hydroxy carbonyl compounds",

abstract = "A procedure has been developed for direct, asymmetric aldol reactions of α,α-dialkyl aldehydes with aromatic aldehydes, which produces quaternary carbon-containing β-hydroxy carbonyl compounds. The processes, promoted by the organocatalyst (S) pyrrolidine sulfonamide, take place in high yields with exceptionally high levels of enantioselectivities.",

keywords = "Aldehyde, Aldol reaction, Asymmetric catalysis, Organocatalyst, Pyrrolidine sulfonamide",

author = "Wei Wang and Hao Li and Jian Wang",

note = "Funding Information: Financial support from the Department of Chemistry and the Research Allocation Committee, University of New Mexico, is greatly acknowledged. We thank Professor Patrick S. Mariano for making critical editorial comments about the manuscript. ",

year = "2005",

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doi = "10.1016/j.tetlet.2005.05.067",

language = "English (US)",

volume = "46",

pages = "5077--5079",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Direct, pyrrolidine sulfonamide promoted enantioselective aldol reactions of α,α-dialkyl aldehydes

T2 - Synthesis of quaternary carbon-containing β-hydroxy carbonyl compounds

AU - Wang, Wei

AU - Li, Hao

AU - Wang, Jian

N1 - Funding Information: Financial support from the Department of Chemistry and the Research Allocation Committee, University of New Mexico, is greatly acknowledged. We thank Professor Patrick S. Mariano for making critical editorial comments about the manuscript.

PY - 2005/7/25

Y1 - 2005/7/25

N2 - A procedure has been developed for direct, asymmetric aldol reactions of α,α-dialkyl aldehydes with aromatic aldehydes, which produces quaternary carbon-containing β-hydroxy carbonyl compounds. The processes, promoted by the organocatalyst (S) pyrrolidine sulfonamide, take place in high yields with exceptionally high levels of enantioselectivities.

AB - A procedure has been developed for direct, asymmetric aldol reactions of α,α-dialkyl aldehydes with aromatic aldehydes, which produces quaternary carbon-containing β-hydroxy carbonyl compounds. The processes, promoted by the organocatalyst (S) pyrrolidine sulfonamide, take place in high yields with exceptionally high levels of enantioselectivities.

KW - Aldehyde

KW - Aldol reaction

KW - Asymmetric catalysis

KW - Organocatalyst

KW - Pyrrolidine sulfonamide

UR - http://www.scopus.com/inward/record.url?scp=20544474258&partnerID=8YFLogxK

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DO - 10.1016/j.tetlet.2005.05.067

M3 - Article

AN - SCOPUS:20544474258

SN - 0040-4039

VL - 46

SP - 5077

EP - 5079

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

Direct, pyrrolidine sulfonamide promoted enantioselective aldol reactions of α,α-dialkyl aldehydes: Synthesis of quaternary carbon-containing β-hydroxy carbonyl compounds

Abstract

Keywords

ASJC Scopus subject areas

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