Synthesis of tertiary α-hydroxy acids by silylene transfer to α-keto esters

Brett E. Howard; K. A. Woerpel

doi:10.1021/ol702148x

Synthesis of tertiary α-hydroxy acids by silylene transfer to α-keto esters

Brett E. Howard, K. A. Woerpel

Chemistry

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

Abstract

(Chemical Equation Presented) α-Keto esters can be converted into α-hydroxy acids in a single flask involving metal-catalyzed silylene transfer, 6π-electrocyclization, Ireland-Claisen rearrangement, and hydrolysis. This reaction sequence is stereoselective and tolerates alkyl- and aryl-substituted α-keto ester substrates as well as an α-imino ester.

Original language	English (US)
Pages (from-to)	4651-4653
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	22
DOIs	https://doi.org/10.1021/ol702148x
State	Published - Oct 25 2007

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol702148x

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title = "Synthesis of tertiary α-hydroxy acids by silylene transfer to α-keto esters",

abstract = "(Chemical Equation Presented) α-Keto esters can be converted into α-hydroxy acids in a single flask involving metal-catalyzed silylene transfer, 6π-electrocyclization, Ireland-Claisen rearrangement, and hydrolysis. This reaction sequence is stereoselective and tolerates alkyl- and aryl-substituted α-keto ester substrates as well as an α-imino ester.",

author = "Howard, {Brett E.} and Woerpel, {K. A.}",

year = "2007",

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doi = "10.1021/ol702148x",

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AU - Woerpel, K. A.

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N2 - (Chemical Equation Presented) α-Keto esters can be converted into α-hydroxy acids in a single flask involving metal-catalyzed silylene transfer, 6π-electrocyclization, Ireland-Claisen rearrangement, and hydrolysis. This reaction sequence is stereoselective and tolerates alkyl- and aryl-substituted α-keto ester substrates as well as an α-imino ester.

AB - (Chemical Equation Presented) α-Keto esters can be converted into α-hydroxy acids in a single flask involving metal-catalyzed silylene transfer, 6π-electrocyclization, Ireland-Claisen rearrangement, and hydrolysis. This reaction sequence is stereoselective and tolerates alkyl- and aryl-substituted α-keto ester substrates as well as an α-imino ester.

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Synthesis of tertiary α-hydroxy acids by silylene transfer to α-keto esters

Abstract

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