Work

Chiral Potassium Brønsted Base‐Catalyzed Stereoselective Synthesis of 1,3‐Diols via a Tandem Allylic Isomerization/Asymmetric Aldol–Tishchenko Reaction

Year: 2025

Type: article

Abstract: A series of chiral potassium Brønsted bases containing 3,3′‐substituted 1,1′‐bi‐2‐naphthol‐based chiral crown ethers are demonstrated as sustainable metal catalysts for a tandem allylic isomerization/asymmetric aldol–Tishchenko reaction. The crown ether creates an effective chiral environment around the potassium cation, yielding diverse 1,3‐diols containing three contiguous stereogenic centers with excellent diastereoselectivity and high enantioselectivity. This system allows the use of allylic alcohols instead of enolizable ketones as nucleophiles, thus broadening the synthetic applicability of this reaction.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.70108

Authors: Hiroki Ishikawa, Masahiro Sai

Institutions: Gifu University, Shimane University, Research Foundation ITSUU Laboratory

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,650