Combined carbometalation-zinc homologation-allylation reactions as a new approach for alkoxyallylation of aldehydes

Tom Mejuch; Mark Botoshansky; Ilan Marek

doi:10.1021/ol201221d

Combined carbometalation-zinc homologation-allylation reactions as a new approach for alkoxyallylation of aldehydes

Tom Mejuch, Mark Botoshansky, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

The combined carbometalation reaction of ynol ethers followed by a zinc homologation and further allylation reactions lead to an efficient preparation of allylic vicinal diols. The stereochemical outcome of the reaction shows that the substituent of the aldehyde occupies a pseudoaxial position in a Zimmerman-Traxler transition state.

Original language	English
Pages (from-to)	3604-3607
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	14
DOIs	https://doi.org/10.1021/ol201221d
State	Published - 15 Jul 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol201221d

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title = "Combined carbometalation-zinc homologation-allylation reactions as a new approach for alkoxyallylation of aldehydes",

abstract = "The combined carbometalation reaction of ynol ethers followed by a zinc homologation and further allylation reactions lead to an efficient preparation of allylic vicinal diols. The stereochemical outcome of the reaction shows that the substituent of the aldehyde occupies a pseudoaxial position in a Zimmerman-Traxler transition state.",

author = "Tom Mejuch and Mark Botoshansky and Ilan Marek",

year = "2011",

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doi = "10.1021/ol201221d",

language = "الإنجليزيّة",

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journal = "Organic Letters",

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T1 - Combined carbometalation-zinc homologation-allylation reactions as a new approach for alkoxyallylation of aldehydes

AU - Mejuch, Tom

AU - Botoshansky, Mark

AU - Marek, Ilan

PY - 2011/7/15

Y1 - 2011/7/15

N2 - The combined carbometalation reaction of ynol ethers followed by a zinc homologation and further allylation reactions lead to an efficient preparation of allylic vicinal diols. The stereochemical outcome of the reaction shows that the substituent of the aldehyde occupies a pseudoaxial position in a Zimmerman-Traxler transition state.

AB - The combined carbometalation reaction of ynol ethers followed by a zinc homologation and further allylation reactions lead to an efficient preparation of allylic vicinal diols. The stereochemical outcome of the reaction shows that the substituent of the aldehyde occupies a pseudoaxial position in a Zimmerman-Traxler transition state.

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U2 - 10.1021/ol201221d

DO - 10.1021/ol201221d

M3 - مقالة

SN - 1523-7060

VL - 13

SP - 3604

EP - 3607

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

Combined carbometalation-zinc homologation-allylation reactions as a new approach for alkoxyallylation of aldehydes

Abstract

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