Triarylcarbenium ions as catalysts in the Mukaiyama Aldol addition: A mechanistic investigation

Scott E. Denmark; Chien Tien Chen

doi:10.1016/S0040-4039(00)73345-4

Triarylcarbenium ions as catalysts in the Mukaiyama Aldol addition: A mechanistic investigation

Scott E. Denmark, Chien Tien Chen

Chemistry

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

Abstract

1-Phenyl-2:3,6:7-dibenzosuberyl salts 5⁺ efficiently catalyze the aldol reaction between silyl enol ethers and benzaldehyde with moderate diastereoselectivity. Crossover experiments with doubly labeled silyl enol ethers, kinetic and stereochemical studies identify 5⁺ as the catalyst rather than a Lewis acidic R₃SiX species in this transformation.

Original language	English (US)
Pages (from-to)	4327-4330
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4039(00)73345-4
State	Published - Jun 20 1994

Keywords

Aldol Condensation
Diastereoselective
Triarylcarbenium ions

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Online availability

10.1016/S0040-4039(00)73345-4

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title = "Triarylcarbenium ions as catalysts in the Mukaiyama Aldol addition: A mechanistic investigation",

abstract = "1-Phenyl-2:3,6:7-dibenzosuberyl salts 5+ efficiently catalyze the aldol reaction between silyl enol ethers and benzaldehyde with moderate diastereoselectivity. Crossover experiments with doubly labeled silyl enol ethers, kinetic and stereochemical studies identify 5+ as the catalyst rather than a Lewis acidic R3SiX species in this transformation.",

keywords = "Aldol Condensation, Diastereoselective, Triarylcarbenium ions",

author = "Denmark, {Scott E.} and Chen, {Chien Tien}",

year = "1994",

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doi = "10.1016/S0040-4039(00)73345-4",

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journal = "Tetrahedron Letters",

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T2 - A mechanistic investigation

AU - Denmark, Scott E.

AU - Chen, Chien Tien

PY - 1994/6/20

Y1 - 1994/6/20

N2 - 1-Phenyl-2:3,6:7-dibenzosuberyl salts 5+ efficiently catalyze the aldol reaction between silyl enol ethers and benzaldehyde with moderate diastereoselectivity. Crossover experiments with doubly labeled silyl enol ethers, kinetic and stereochemical studies identify 5+ as the catalyst rather than a Lewis acidic R3SiX species in this transformation.

AB - 1-Phenyl-2:3,6:7-dibenzosuberyl salts 5+ efficiently catalyze the aldol reaction between silyl enol ethers and benzaldehyde with moderate diastereoselectivity. Crossover experiments with doubly labeled silyl enol ethers, kinetic and stereochemical studies identify 5+ as the catalyst rather than a Lewis acidic R3SiX species in this transformation.

KW - Aldol Condensation

KW - Diastereoselective

KW - Triarylcarbenium ions

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Triarylcarbenium ions as catalysts in the Mukaiyama Aldol addition: A mechanistic investigation

Abstract

Keywords

ASJC Scopus subject areas

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