Preparation and Reactivity of Acyclic Chiral Allylzinc Species by a Zinc-Brook Rearrangement

Markus Leibeling; Khriesto A. Shurrush; Veronika Werner; Lionel Perrin; Ilan Marek

doi:10.1002/anie.201602393

Preparation and Reactivity of Acyclic Chiral Allylzinc Species by a Zinc-Brook Rearrangement

Markus Leibeling, Khriesto A. Shurrush, Veronika Werner, Lionel Perrin, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

The zinc-Brook rearrangement of enantiomerically enriched α-hydroxy allylsilane produces a chiral allylzinc intermediate, which reacts with retention of configuration in the presence of an electrophile. Two remarkable features of this transformation are the stereochemical outcome during the formation of the allylzinc species and the complete stereocontrol in the organized six-membered transition state, which leads to an overall and complete transfer of chirality within the reaction sequence.

Original language	English
Pages (from-to)	6057-6061
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	20
DOIs	https://doi.org/10.1002/anie.201602393
State	Published - 10 May 2016

Keywords

Brook rearrangement
allylic compounds
chirality
olefins
zinc

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

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10.1002/anie.201602393

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title = "Preparation and Reactivity of Acyclic Chiral Allylzinc Species by a Zinc-Brook Rearrangement",

abstract = "The zinc-Brook rearrangement of enantiomerically enriched α-hydroxy allylsilane produces a chiral allylzinc intermediate, which reacts with retention of configuration in the presence of an electrophile. Two remarkable features of this transformation are the stereochemical outcome during the formation of the allylzinc species and the complete stereocontrol in the organized six-membered transition state, which leads to an overall and complete transfer of chirality within the reaction sequence.",

keywords = "Brook rearrangement, allylic compounds, chirality, olefins, zinc",

author = "Markus Leibeling and Shurrush, {Khriesto A.} and Veronika Werner and Lionel Perrin and Ilan Marek",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

month = may,

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doi = "10.1002/anie.201602393",

language = "الإنجليزيّة",

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T1 - Preparation and Reactivity of Acyclic Chiral Allylzinc Species by a Zinc-Brook Rearrangement

AU - Leibeling, Markus

AU - Shurrush, Khriesto A.

AU - Werner, Veronika

AU - Perrin, Lionel

AU - Marek, Ilan

PY - 2016/5/10

Y1 - 2016/5/10

N2 - The zinc-Brook rearrangement of enantiomerically enriched α-hydroxy allylsilane produces a chiral allylzinc intermediate, which reacts with retention of configuration in the presence of an electrophile. Two remarkable features of this transformation are the stereochemical outcome during the formation of the allylzinc species and the complete stereocontrol in the organized six-membered transition state, which leads to an overall and complete transfer of chirality within the reaction sequence.

AB - The zinc-Brook rearrangement of enantiomerically enriched α-hydroxy allylsilane produces a chiral allylzinc intermediate, which reacts with retention of configuration in the presence of an electrophile. Two remarkable features of this transformation are the stereochemical outcome during the formation of the allylzinc species and the complete stereocontrol in the organized six-membered transition state, which leads to an overall and complete transfer of chirality within the reaction sequence.

KW - Brook rearrangement

KW - allylic compounds

KW - chirality

KW - olefins

KW - zinc

UR - http://www.scopus.com/inward/record.url?scp=84963808625&partnerID=8YFLogxK

U2 - 10.1002/anie.201602393

DO - 10.1002/anie.201602393

M3 - مقالة

SN - 1433-7851

VL - 55

SP - 6057

EP - 6061

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 20

ER -

Preparation and Reactivity of Acyclic Chiral Allylzinc Species by a Zinc-Brook Rearrangement

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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