A PTC-catalyzed diastereoselective Mannich reaction to access indanone-based α-amino acid derivatives.

Authors

Lei Yang, Yu-Ting Hou, Wan-Yu Wei, Yi-Ping Liu, Lin Chen, Wei-Cheng Yuan, Jian-Qiang Zhao

Published in

Organic & biomolecular chemistry. Oct 09, 2026. Epub Oct 09, 2026.

Abstract

We herein disclose a phase-transfer-catalyzed diastereoselective Mannich reaction between β,γ-alkynyl-α-ketimines and in situ generated 1-hydroxy isobenzofulvene anions from 2-alkylidene-1-indanones, enabling the formation of indanone-based α-amino acid derivatives with good results (up to 93% yield with >20 : 1 dr in all cases). The protocol is characterized by mild reaction conditions, broad substrate tolerance, and excellent diastereoselectivity. The practicality of the methodology is underscored by a gram-scale experiment and the coupling of the product with structurally complex pharmaceuticals. Notably, this work represents the first example of a reaction of 1-hydroxyl isobenzofulvene anions with imines.

PMID:
42853022
Bibliographic data and abstract were imported from PubMed on 09 Oct 2026.

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