Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters

Xu Chen; Kaushalendra Patel; Ilan Marek

doi:10.1002/anie.202212425

Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters

Xu Chen
, Kaushalendra Patel
, Ilan Marek

Chemistry

Technion - Israel Institute of Technology

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

Abstract

An efficient method for the stereoselective construction of tertiary C−O bonds via a stereoinvertive nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl carbinol derivatives using water, alcohols and phenols as nucleophiles has been developed. This substitution reaction proceeds under mild conditions and tolerates several functional groups, providing a new access to the stereoselective formation of highly congested tertiary homoallyl alcohols and ethers.

Original language	English
Article number	e202212425
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	3
DOIs	https://doi.org/10.1002/anie.202212425
State	Published - 16 Jan 2023

Keywords

Allylic Compounds
Cyclopropanes
Nucleophilic Substitution
Stereoinvertion
Synthetic Methods

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.202212425

Cite this

@article{757013bb02234fa6bc5f2de6f1ca61ed,

title = "Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters",

abstract = "An efficient method for the stereoselective construction of tertiary C−O bonds via a stereoinvertive nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl carbinol derivatives using water, alcohols and phenols as nucleophiles has been developed. This substitution reaction proceeds under mild conditions and tolerates several functional groups, providing a new access to the stereoselective formation of highly congested tertiary homoallyl alcohols and ethers.",

keywords = "Allylic Compounds, Cyclopropanes, Nucleophilic Substitution, Stereoinvertion, Synthetic Methods",

author = "Xu Chen and Kaushalendra Patel and Ilan Marek",

note = "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: {\textcopyright} 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

year = "2023",

month = jan,

day = "16",

doi = "10.1002/anie.202212425",

language = "English",

volume = "62",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Inc.",

number = "3",

}

TY - JOUR

T1 - Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters

AU - Chen, Xu

AU - Patel, Kaushalendra

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 - 2023/1/16

Y1 - 2023/1/16

N2 - An efficient method for the stereoselective construction of tertiary C−O bonds via a stereoinvertive nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl carbinol derivatives using water, alcohols and phenols as nucleophiles has been developed. This substitution reaction proceeds under mild conditions and tolerates several functional groups, providing a new access to the stereoselective formation of highly congested tertiary homoallyl alcohols and ethers.

AB - An efficient method for the stereoselective construction of tertiary C−O bonds via a stereoinvertive nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl carbinol derivatives using water, alcohols and phenols as nucleophiles has been developed. This substitution reaction proceeds under mild conditions and tolerates several functional groups, providing a new access to the stereoselective formation of highly congested tertiary homoallyl alcohols and ethers.

KW - Allylic Compounds

KW - Cyclopropanes

KW - Nucleophilic Substitution

KW - Stereoinvertion

KW - Synthetic Methods

UR - https://www.scopus.com/pages/publications/85143842248

U2 - 10.1002/anie.202212425

DO - 10.1002/anie.202212425

M3 - Article

C2 - 36413111

SN - 1433-7851

VL - 62

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 3

M1 - e202212425

ER -

Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this