Achiral 2‐pyridone and 4‐aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals-Reference-Cited by-同舟云学术

Achiral 2‐pyridone and 4‐aminopyridine act as chiral inducers of asymmetric autocatalysis with amplification of enantiomeric excess via the formation of chiral crystals

Published:2023-08-24 Issue:1 Volume:36 Page:
ISSN:0899-0042
Container-title:Chirality
language:en
Short-container-title:Chirality

Author:

Matsumoto Arimasa¹,Tateishi Daisuke²,Nakajima Tsuyoshi²,Kurosaki Shiori²,Ogawa Tomohiro²,Kawasaki Tsuneomi²^ORCID,Soai Kenso²³

Affiliation:

1. Department of Chemistry, Biology, and Environmental Science Nara Women's University Nara Japan

2. Department of Applied Chemistry Tokyo University of Science Tokyo Japan

3. Research Organization for Nano & Life Innovation Waseda University Tokyo Japan

Abstract

AbstractEnantiomorphous crystals of achiral 2‐pyridone and 4‐aminopyridine served as sources of chirality, to induce the asymmetric autocatalysis of 5‐pyrimidyl alkanol during the asymmetric addition of diisopropylzinc to the corresponding pyrimidine‐5‐carbaldehyde, that is, the Soai reaction. Following a significant amplification of enantiomeric excess through asymmetric autocatalysis, highly enantioenriched 5‐pyrimidyl alkanol could be synthesized with their corresponding absolute configurations to those of chiral crystals of 2‐pyridone and 4‐aminopyridine.

Funder

Japan Society for the Promotion of Science

Ministry of Education, Culture, Sports, Science and Technology

Publisher

Wiley

Subject

Organic Chemistry,Spectroscopy,Drug Discovery,Pharmacology,Catalysis,Analytical Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.23617

Reference81 articles.

1. Crystalline Architectures as Templates of Relevance to the Origins of Homochirality

2. Chiral Symmetry Breaking in Sodium Chlorate Crystallization

3. Absolute Asymmetric Synthesis: The Origin, Control, and Amplification of Chirality

4. By-design enantioselective self-amplification based on non-covalent product–catalyst interactions

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