Kinetic resolution of racemic tertiary allylic alcohols through S<sub>N</sub>2′ reaction using a chiral bisphosphoric acid/silver(<scp>i</scp>) salt co-catalyst system-Reference-Cited by-同舟云学术

Kinetic resolution of racemic tertiary allylic alcohols through S_N2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system

Published:2022 Issue:33 Volume:13 Page:9607-9613
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Kayal Satavisha¹,Kikuchi Jun¹^ORCID,Shinagawa Naoya¹,Umemiya Shigenobu¹^ORCID,Terada Masahiro¹^ORCID

Affiliation:

1. Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

A highly efficient KR of racemic tertiary allylic alcohols was developed through the intramolecular SN2′ reaction using the chiral bisphosphoric acid/silver carbonate co-catalyst system, affording cis-epoxides and recovered alcohols in a high s-factor.

Funder

Ministry of Education, Culture, Sports, Science and Technology

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/SC/D2SC03052G

Reference63 articles.

1. Quaternary Stereocenters, Challenges and Solutions for Organic Synthesis , ed. J. Christoffers and A. Baro , Wiley-VCH , Weinheim , 2005

2. Science of Synthesis: Stereoselective Synthesis Vol. 2: Stereoselective Reactions of Carbonyl and Imino Groups , ed. G. A. Molander , P. A. Evans and J. G. de Vries , Georg Thieme Verlag KG : New York , 2010

3. Catalytic Asymmetric Organozinc Additions to Carbonyl Compounds

4. Asymmetric Synthesis of Tertiary Alcohols and α-Tertiary Amines via Cu-Catalyzed C−C Bond Formation to Ketones and Ketimines

5. Recent Advances in Catalytic Asymmetric Synthesis of Tertiary Alcohols via Nucleophilic Addition to Ketones

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