Pd-Catalyzed Selective Remote Ring Opening of Polysubstituted Cyclopropanols

Sukhdev Singh; Marwan Simaan; Ilan Marek

doi:https://doi.org/10.1002/chem.201802016

Pd-Catalyzed Selective Remote Ring Opening of Polysubstituted Cyclopropanols

Sukhdev Singh, Marwan Simaan, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

The distant functionalization of ω-ene cyclopropanols is induced by a Pd-catalyzed Heck reaction triggering a “metal-walk” and selective ring-opening of the three-membered ring. This approach provides a new class of acyclic aldehydes possessing concomitantly a stereodefined double bond and a quaternary carbon stereocenter α to the carbonyl group.

Original language	English
Pages (from-to)	8553-8557
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	34
DOIs	https://doi.org/10.1002/chem.201802016
State	Published - 18 Jun 2018

Keywords

cyclopropanol
metal walk
quaternary stereocenters
remote functionalization
stereochemistry

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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https://doi.org/10.1002/chem.201802016

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title = "Pd-Catalyzed Selective Remote Ring Opening of Polysubstituted Cyclopropanols",

abstract = "The distant functionalization of ω-ene cyclopropanols is induced by a Pd-catalyzed Heck reaction triggering a “metal-walk” and selective ring-opening of the three-membered ring. This approach provides a new class of acyclic aldehydes possessing concomitantly a stereodefined double bond and a quaternary carbon stereocenter α to the carbonyl group.",

keywords = "cyclopropanol, metal walk, quaternary stereocenters, remote functionalization, stereochemistry",

author = "Sukhdev Singh and Marwan Simaan and Ilan Marek",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "https://doi.org/10.1002/chem.201802016",

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AU - Singh, Sukhdev

AU - Simaan, Marwan

AU - Marek, Ilan

PY - 2018/6/18

Y1 - 2018/6/18

N2 - The distant functionalization of ω-ene cyclopropanols is induced by a Pd-catalyzed Heck reaction triggering a “metal-walk” and selective ring-opening of the three-membered ring. This approach provides a new class of acyclic aldehydes possessing concomitantly a stereodefined double bond and a quaternary carbon stereocenter α to the carbonyl group.

AB - The distant functionalization of ω-ene cyclopropanols is induced by a Pd-catalyzed Heck reaction triggering a “metal-walk” and selective ring-opening of the three-membered ring. This approach provides a new class of acyclic aldehydes possessing concomitantly a stereodefined double bond and a quaternary carbon stereocenter α to the carbonyl group.

KW - cyclopropanol

KW - metal walk

KW - quaternary stereocenters

KW - remote functionalization

KW - stereochemistry

UR - http://www.scopus.com/inward/record.url?scp=85047449356&partnerID=8YFLogxK

U2 - https://doi.org/10.1002/chem.201802016

DO - https://doi.org/10.1002/chem.201802016

M3 - مقالة

SN - 0947-6539

VL - 24

SP - 8553

EP - 8557

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 34

ER -

Pd-Catalyzed Selective Remote Ring Opening of Polysubstituted Cyclopropanols

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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