Solvent-triggered stereoselectivity of α,α-cyclopropanation of amino acids in the Ni(ii) chiral coordination environment-Reference-Cited by-同舟云学术

Solvent-triggered stereoselectivity of α,α-cyclopropanation of amino acids in the Ni(ii) chiral coordination environment

Published:2020 Issue:25 Volume:49 Page:8636-8644
ISSN:1477-9226
Container-title:Dalton Transactions
language:en
Short-container-title:Dalton Trans.

Author:

Levitskiy Oleg A.¹²³⁴,Aglamazova Olga I.¹²³⁴,Grishin Yuri K.¹²³⁴,Paseshnichenko Ksenia A.¹²³⁴^ORCID,Soloshonok Vadim A.⁵⁶⁷⁸⁹,Moriwaki Hiroki¹⁰¹¹¹²,Magdesieva Tatiana V.¹²³⁴^ORCID

Affiliation:

1. Lomonosov Moscow State University

2. Dept. of Chemistry

3. Moscow 119991

4. Russia

5. Department of Organic Chemistry I

6. Faculty of Chemistry

7. University of Basque Country UPV/EHU

8. 20018 San Sebastian

9. Spain

10. Hamari Chemical Ltd

11. Osaka 533-0024

12. Japan

Abstract

Unexpected solvent-controlled increase in stereoselectivity of glycine cyclopropanation within chiral Ni(ii) coordination environment was observed and rationalized. Cyclopropanated diastereomeric complexes exhibit stereodependent redox-activity.

Funder

Russian Foundation for Basic Research

Publisher

Royal Society of Chemistry (RSC)

Subject

Inorganic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/DT/D0DT01578D

Reference29 articles.

1. Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases; Part 1: alkyl halide alkylations

2. Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: Aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of α-amino acids

3. Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations