A New Procedure for the One-Carbon Homologation of Ketones to α-Hydroxy Aldehydes

Maciej Adamczyk; E. Kurt Dolence; David Watt; M. Robert Christy; Joseph H. Reibenspies; Oren P. Anderson

doi:10.1021/jo00182a012

A New Procedure for the One-Carbon Homologation of Ketones to α-Hydroxy Aldehydes

Maciej Adamczyk, E. Kurt Dolence, David Watt, M. Robert Christy, Joseph H. Reibenspies, Oren P. Anderson

Molecular and Cellular Biochemistry

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

39 Scopus citations

Abstract

A new, one-carbon homologation procedure for the conversion of ketones to-hydroxy aldehydes involves two steps: (1) Darzens condensation of ketones with chloromethyl phenyl sulfone; (2) ring opening of the intermediate α,β-epoxy sulfones with hydroxide ion generated by adding water to potassium tert-butoxide. This new sequence proceeds in good overall yields and with high stereoselectivity.

Original language	English
Pages (from-to)	1378-1382
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	49
Issue number	8
DOIs	https://doi.org/10.1021/jo00182a012
State	Published - Nov 1984

ASJC Scopus subject areas

Organic Chemistry

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abstract = "A new, one-carbon homologation procedure for the conversion of ketones to-hydroxy aldehydes involves two steps: (1) Darzens condensation of ketones with chloromethyl phenyl sulfone; (2) ring opening of the intermediate α,β-epoxy sulfones with hydroxide ion generated by adding water to potassium tert-butoxide. This new sequence proceeds in good overall yields and with high stereoselectivity.",

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AU - Adamczyk, Maciej

AU - Kurt Dolence, E.

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AU - Christy, M. Robert

AU - Reibenspies, Joseph H.

AU - Anderson, Oren P.

PY - 1984/11

Y1 - 1984/11

N2 - A new, one-carbon homologation procedure for the conversion of ketones to-hydroxy aldehydes involves two steps: (1) Darzens condensation of ketones with chloromethyl phenyl sulfone; (2) ring opening of the intermediate α,β-epoxy sulfones with hydroxide ion generated by adding water to potassium tert-butoxide. This new sequence proceeds in good overall yields and with high stereoselectivity.

AB - A new, one-carbon homologation procedure for the conversion of ketones to-hydroxy aldehydes involves two steps: (1) Darzens condensation of ketones with chloromethyl phenyl sulfone; (2) ring opening of the intermediate α,β-epoxy sulfones with hydroxide ion generated by adding water to potassium tert-butoxide. This new sequence proceeds in good overall yields and with high stereoselectivity.

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A New Procedure for the One-Carbon Homologation of Ketones to α-Hydroxy Aldehydes

Abstract

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