Enantiomerically pure cyclopropenylcarbinols as a source of chiral alkylidenecyclopropane derivatives

Samah Simaan; Ahmad Masarwa; Philippe Bertus; Ilan Marek

doi:10.1002/anie.200600556

Enantiomerically pure cyclopropenylcarbinols as a source of chiral alkylidenecyclopropane derivatives

Samah Simaan^*, Ahmad Masarwa, Philippe Bertus, Ilan Marek

^*Corresponding author for this work

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

82 Scopus citations

Abstract

(Chemical Equation Presented) The straightforward approach: The copper-catalyzed carbomagnesiation reaction of chiral cyclopropenylcarbinol derivatives, obtained through kinetic resolution of secondary allylic alcohols, leads to the preparation of enantiomerically pure alkylidenecyclopropane derivatives. The reaction mechanism is composed of a syn carbometalation followed by a syn elimination reaction.

Original language	English
Pages (from-to)	3963-3965
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	24
DOIs	https://doi.org/10.1002/anie.200600556
State	Published - 12 Jun 2006
Externally published	Yes

Keywords

Cyclopropanes
Elimination
Grignard reagents
Homogeneous catalysis
Strained molecules

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10.1002/anie.200600556

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abstract = "(Chemical Equation Presented) The straightforward approach: The copper-catalyzed carbomagnesiation reaction of chiral cyclopropenylcarbinol derivatives, obtained through kinetic resolution of secondary allylic alcohols, leads to the preparation of enantiomerically pure alkylidenecyclopropane derivatives. The reaction mechanism is composed of a syn carbometalation followed by a syn elimination reaction.",

keywords = "Cyclopropanes, Elimination, Grignard reagents, Homogeneous catalysis, Strained molecules",

author = "Samah Simaan and Ahmad Masarwa and Philippe Bertus and Ilan Marek",

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AU - Simaan, Samah

AU - Masarwa, Ahmad

AU - Bertus, Philippe

AU - Marek, Ilan

PY - 2006/6/12

Y1 - 2006/6/12

N2 - (Chemical Equation Presented) The straightforward approach: The copper-catalyzed carbomagnesiation reaction of chiral cyclopropenylcarbinol derivatives, obtained through kinetic resolution of secondary allylic alcohols, leads to the preparation of enantiomerically pure alkylidenecyclopropane derivatives. The reaction mechanism is composed of a syn carbometalation followed by a syn elimination reaction.

AB - (Chemical Equation Presented) The straightforward approach: The copper-catalyzed carbomagnesiation reaction of chiral cyclopropenylcarbinol derivatives, obtained through kinetic resolution of secondary allylic alcohols, leads to the preparation of enantiomerically pure alkylidenecyclopropane derivatives. The reaction mechanism is composed of a syn carbometalation followed by a syn elimination reaction.

KW - Cyclopropanes

KW - Elimination

KW - Grignard reagents

KW - Homogeneous catalysis

KW - Strained molecules

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SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 24

ER -

Enantiomerically pure cyclopropenylcarbinols as a source of chiral alkylidenecyclopropane derivatives

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