A mild oxidation of 1,1-diorganometallics to ketones and aldehydes. A new stereoselective approach to aldol products part I

Paul Knochel; Chaodong Xiao; Ming Chang P. Yeh

doi:10.1016/S0040-4039(00)82431-4

A mild oxidation of 1,1-diorganometallics to ketones and aldehydes. A new stereoselective approach to aldol products part I

Paul Knochel^*
, Chaodong Xiao
, Ming Chang P. Yeh

^*Corresponding author for this work

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

42 Citations (Scopus)

Abstract

The 1,1-diorganometallics of magnesium and zinc 1 are converted by the reaction with Me₃SnCl to the 1,1-diorganometallics of tin and zinc 2 which are readily oxidized by dry air at -10° to 0°C to afford the corresponding aldehydes and ketones 3 in 57-91% yield. This mild oxidation reaction allows a new stereoselective approach to aldol products. An extension of the reaction to 1,1-diorganometallics of silicon and zinc is described.

Original language	English
Pages (from-to)	6697-6700
Number of pages	4
Journal	Tetrahedron Letters
Volume	29
Issue number	51
DOIs	https://doi.org/10.1016/S0040-4039(00)82431-4
Publication status	Published - 1988
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)82431-4

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abstract = "The 1,1-diorganometallics of magnesium and zinc 1 are converted by the reaction with Me3SnCl to the 1,1-diorganometallics of tin and zinc 2 which are readily oxidized by dry air at -10° to 0°C to afford the corresponding aldehydes and ketones 3 in 57-91\% yield. This mild oxidation reaction allows a new stereoselective approach to aldol products. An extension of the reaction to 1,1-diorganometallics of silicon and zinc is described.",

author = "Paul Knochel and Chaodong Xiao and Yeh, \{Ming Chang P.\}",

year = "1988",

doi = "10.1016/S0040-4039(00)82431-4",

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pages = "6697--6700",

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T1 - A mild oxidation of 1,1-diorganometallics to ketones and aldehydes. A new stereoselective approach to aldol products part I

AU - Knochel, Paul

AU - Xiao, Chaodong

AU - Yeh, Ming Chang P.

PY - 1988

Y1 - 1988

N2 - The 1,1-diorganometallics of magnesium and zinc 1 are converted by the reaction with Me3SnCl to the 1,1-diorganometallics of tin and zinc 2 which are readily oxidized by dry air at -10° to 0°C to afford the corresponding aldehydes and ketones 3 in 57-91% yield. This mild oxidation reaction allows a new stereoselective approach to aldol products. An extension of the reaction to 1,1-diorganometallics of silicon and zinc is described.

AB - The 1,1-diorganometallics of magnesium and zinc 1 are converted by the reaction with Me3SnCl to the 1,1-diorganometallics of tin and zinc 2 which are readily oxidized by dry air at -10° to 0°C to afford the corresponding aldehydes and ketones 3 in 57-91% yield. This mild oxidation reaction allows a new stereoselective approach to aldol products. An extension of the reaction to 1,1-diorganometallics of silicon and zinc is described.

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UR - https://www.scopus.com/pages/publications/0002729418#tab=citedBy

U2 - 10.1016/S0040-4039(00)82431-4

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M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

A mild oxidation of 1,1-diorganometallics to ketones and aldehydes. A new stereoselective approach to aldol products part I

Abstract

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