Axial preferences in allylations via the Zimmerman-Traxler transition state

Noga Gilboa; Hao Wang; Kendall N. Houk; Ilan Marek

doi:10.1002/chem.201101049

Axial preferences in allylations via the Zimmerman-Traxler transition state

Noga Gilboa, Hao Wang, Kendall N. Houk, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

On the other side of the Traxler? The stereochemical outcome of the allylation reaction of 3,3-disubstituted allylzinc species with aldehydes shows that the aryl or alkyl group of the electrophilic carbonyl reactant occupies a pseudoaxial position in the Zimmerman-Traxler transition state to avoid gauche interactions (see scheme).

Original language	English
Pages (from-to)	8000-8004
Number of pages	5
Journal	Chemistry - A European Journal
Volume	17
Issue number	29
DOIs	https://doi.org/10.1002/chem.201101049
State	Published - 11 Jul 2011

Keywords

allylic compounds
asymmetric synthesis
carbenoids
carbometalation
transition states
zinc

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1002/chem.201101049

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title = "Axial preferences in allylations via the Zimmerman-Traxler transition state",

abstract = "On the other side of the Traxler? The stereochemical outcome of the allylation reaction of 3,3-disubstituted allylzinc species with aldehydes shows that the aryl or alkyl group of the electrophilic carbonyl reactant occupies a pseudoaxial position in the Zimmerman-Traxler transition state to avoid gauche interactions (see scheme).",

keywords = "allylic compounds, asymmetric synthesis, carbenoids, carbometalation, transition states, zinc",

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year = "2011",

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AU - Gilboa, Noga

AU - Wang, Hao

AU - Houk, Kendall N.

AU - Marek, Ilan

PY - 2011/7/11

Y1 - 2011/7/11

N2 - On the other side of the Traxler? The stereochemical outcome of the allylation reaction of 3,3-disubstituted allylzinc species with aldehydes shows that the aryl or alkyl group of the electrophilic carbonyl reactant occupies a pseudoaxial position in the Zimmerman-Traxler transition state to avoid gauche interactions (see scheme).

AB - On the other side of the Traxler? The stereochemical outcome of the allylation reaction of 3,3-disubstituted allylzinc species with aldehydes shows that the aryl or alkyl group of the electrophilic carbonyl reactant occupies a pseudoaxial position in the Zimmerman-Traxler transition state to avoid gauche interactions (see scheme).

KW - allylic compounds

KW - asymmetric synthesis

KW - carbenoids

KW - carbometalation

KW - transition states

KW - zinc

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DO - 10.1002/chem.201101049

M3 - مقالة

SN - 0947-6539

VL - 17

SP - 8000

EP - 8004

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 29

ER -

Axial preferences in allylations via the Zimmerman-Traxler transition state

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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