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

Producción científica: Article › revisión exhaustiva

40 Citas (Scopus)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	1378-1382
Número de páginas	5
Publicación	Journal of Organic Chemistry
Volumen	49
N.º	8
DOI	https://doi.org/10.1021/jo00182a012
Estado	Published - nov 1984

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00182a012

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title = "A New Procedure for the One-Carbon Homologation of Ketones to α-Hydroxy Aldehydes",

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.

AU - Watt, David

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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UR - https://www.scopus.com/pages/publications/0001286952#tab=citedBy

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

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