The Chemistry of Enoxysilacyclobutanes: Highly Selective, Uncatalyzed Aldol Additions

Scott E. Denmark; Brian D. Griedel; Diane M. Coe

doi:10.1021/jo00057a002

The Chemistry of Enoxysilacyclobutanes: Highly Selective, Uncatalyzed Aldol Additions

Scott E. Denmark, Brian D. Griedel, Diane M. Coe

Chemistry

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

Abstract

O-(Silacyclobutyl) ketene acetals derived from esters, thiol esters, and amides reacted with a variety of aldehydes at room temperature without the need for catalysts. The O,O-ketene acetal of E-configuration reacted rapidly to afford the syn aldol products with high diastereoselectivity (93/7∼99/1).

Original language	English (US)
Pages (from-to)	988-990
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	58
Issue number	5
DOIs	https://doi.org/10.1021/jo00057a002
State	Published - 1993

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00057a002

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title = "The Chemistry of Enoxysilacyclobutanes: Highly Selective, Uncatalyzed Aldol Additions",

abstract = "O-(Silacyclobutyl) ketene acetals derived from esters, thiol esters, and amides reacted with a variety of aldehydes at room temperature without the need for catalysts. The O,O-ketene acetal of E-configuration reacted rapidly to afford the syn aldol products with high diastereoselectivity (93/7∼99/1).",

author = "Denmark, {Scott E.} and Griedel, {Brian D.} and Coe, {Diane M.}",

year = "1993",

doi = "10.1021/jo00057a002",

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volume = "58",

pages = "988--990",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "5",

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AU - Griedel, Brian D.

AU - Coe, Diane M.

PY - 1993

Y1 - 1993

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AB - O-(Silacyclobutyl) ketene acetals derived from esters, thiol esters, and amides reacted with a variety of aldehydes at room temperature without the need for catalysts. The O,O-ketene acetal of E-configuration reacted rapidly to afford the syn aldol products with high diastereoselectivity (93/7∼99/1).

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The Chemistry of Enoxysilacyclobutanes: Highly Selective, Uncatalyzed Aldol Additions

Abstract

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