Brook Rearrangement as a Trigger for the Ring Opening of Strained Carbocycles

Fa-Guang Zhang; Guillaume Eppe; Ilan Marek

doi:10.1002/anie.201510094

Brook Rearrangement as a Trigger for the Ring Opening of Strained Carbocycles

Fa-Guang Zhang, Guillaume Eppe, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

The combined regio- and stereoselective carbometalation of cyclopropenyl amides, followed by the addition of an acyl silane, led to the formation of polysubstituted cyclopropyl derivatives as unique diastereoisomers. Upon warming of the reaction mixture to room temperature, a Brook rearrangement proceeded with inversion of configuration to provide ready access to δ-ketoamides possessing a quaternary carbon center with high enantiomeric ratios through selective C-C bond cleavage of the ring.

Original language	English
Pages (from-to)	714-718
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	2
DOIs	https://doi.org/10.1002/anie.201510094
State	Published - 11 Jan 2016

Keywords

Brook rearrangement
one-pot reactions
quaternary carbon centers
strained molecules
synthetic methods

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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10.1002/anie.201510094

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title = "Brook Rearrangement as a Trigger for the Ring Opening of Strained Carbocycles",

abstract = "The combined regio- and stereoselective carbometalation of cyclopropenyl amides, followed by the addition of an acyl silane, led to the formation of polysubstituted cyclopropyl derivatives as unique diastereoisomers. Upon warming of the reaction mixture to room temperature, a Brook rearrangement proceeded with inversion of configuration to provide ready access to δ-ketoamides possessing a quaternary carbon center with high enantiomeric ratios through selective C-C bond cleavage of the ring.",

keywords = "Brook rearrangement, one-pot reactions, quaternary carbon centers, strained molecules, synthetic methods",

author = "Fa-Guang Zhang and Guillaume Eppe and Ilan Marek",

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doi = "10.1002/anie.201510094",

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N2 - The combined regio- and stereoselective carbometalation of cyclopropenyl amides, followed by the addition of an acyl silane, led to the formation of polysubstituted cyclopropyl derivatives as unique diastereoisomers. Upon warming of the reaction mixture to room temperature, a Brook rearrangement proceeded with inversion of configuration to provide ready access to δ-ketoamides possessing a quaternary carbon center with high enantiomeric ratios through selective C-C bond cleavage of the ring.

AB - The combined regio- and stereoselective carbometalation of cyclopropenyl amides, followed by the addition of an acyl silane, led to the formation of polysubstituted cyclopropyl derivatives as unique diastereoisomers. Upon warming of the reaction mixture to room temperature, a Brook rearrangement proceeded with inversion of configuration to provide ready access to δ-ketoamides possessing a quaternary carbon center with high enantiomeric ratios through selective C-C bond cleavage of the ring.

KW - Brook rearrangement

KW - one-pot reactions

KW - quaternary carbon centers

KW - strained molecules

KW - synthetic methods

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M3 - مقالة

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 2

ER -

Brook Rearrangement as a Trigger for the Ring Opening of Strained Carbocycles

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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