Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives

Yogesh Siddaraju; Juliette Sabbatani; Anthony Cohen; Ilan Marek

doi:10.1002/anie.202203652

Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives

Yogesh Siddaraju
, Juliette Sabbatani
, Anthony Cohen
, Ilan Marek

Chemistry

Technion - Israel Institute of Technology

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

Abstract

The diastereoselective double carbometalation reaction of cyclopropenes provides, in a single-pot operation, two ω-ene-[1,1]-bicyclopropyl ester derivatives. One regioisomer then undergoes a Pd-catalyzed addition of aryl iodide to provide skipped dienes possessing several distant stereocenters including two congested quaternary carbon centers with excellent diastereoselectivity.

Original language	English
Article number	e202203652
Journal	Angewandte Chemie - International Edition
Volume	61
Issue number	28
DOIs	https://doi.org/10.1002/anie.202203652
State	Published - 11 Jul 2022

Keywords

Bicyclopropyl Methanol
Carbometallalation
Cyclopropenes
Heck Addition
Quaternary Carbon Stereocenters

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.202203652

Cite this

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title = "Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives",

abstract = "The diastereoselective double carbometalation reaction of cyclopropenes provides, in a single-pot operation, two ω-ene-[1,1]-bicyclopropyl ester derivatives. One regioisomer then undergoes a Pd-catalyzed addition of aryl iodide to provide skipped dienes possessing several distant stereocenters including two congested quaternary carbon centers with excellent diastereoselectivity.",

keywords = "Bicyclopropyl Methanol, Carbometallalation, Cyclopropenes, Heck Addition, Quaternary Carbon Stereocenters",

author = "Yogesh Siddaraju and Juliette Sabbatani and Anthony Cohen and Ilan Marek",

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T1 - Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives

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AU - Sabbatani, Juliette

AU - Cohen, Anthony

AU - Marek, Ilan

N1 - Funding Information: This project has received funding from the European Union's Horizon 2020 research and innovation program under Grant Agreement No. 786976 and from the Israel Science Foundation administrated by the Israel Academy of Sciences and Humanities (Grant No. 487/21). Publisher Copyright: © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

PY - 2022/7/11

Y1 - 2022/7/11

N2 - The diastereoselective double carbometalation reaction of cyclopropenes provides, in a single-pot operation, two ω-ene-[1,1]-bicyclopropyl ester derivatives. One regioisomer then undergoes a Pd-catalyzed addition of aryl iodide to provide skipped dienes possessing several distant stereocenters including two congested quaternary carbon centers with excellent diastereoselectivity.

AB - The diastereoselective double carbometalation reaction of cyclopropenes provides, in a single-pot operation, two ω-ene-[1,1]-bicyclopropyl ester derivatives. One regioisomer then undergoes a Pd-catalyzed addition of aryl iodide to provide skipped dienes possessing several distant stereocenters including two congested quaternary carbon centers with excellent diastereoselectivity.

KW - Bicyclopropyl Methanol

KW - Carbometallalation

KW - Cyclopropenes

KW - Heck Addition

KW - Quaternary Carbon Stereocenters

UR - https://www.scopus.com/pages/publications/85130426134

U2 - 10.1002/anie.202203652

DO - 10.1002/anie.202203652

M3 - Article

SN - 1433-7851

VL - 61

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 28

M1 - e202203652

ER -

Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives

Abstract

Keywords

ASJC Scopus subject areas

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