Cobalt-Stabilized Propargylic Oxocarbenium Ions Enable Direct and Asymmetric Nickel(II) Catalyzed Aldol-Like Reactions
Open Access
- 3 July 2026
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 28 (29) , 9312-9317
Abstract
We describe a direct and asymmetric aldol-like reaction between a wide range of N-acyl-1,3-oxazolidine-2-thiones and cobalt-protected propargylic acetals catalyzed by a chiral nickel(II) complex leading to syn β-alkoxy derivatives. This overcomes longstanding limitations associated with acetals from aliphatic aldehydes, selectively providing syn aldol adducts in excellent yields as single stereoisomers (dr >97:3, er up to >99:1). Furthermore, the cobalt fragment enables downstream intramolecular Pauson-Khand cyclizations, granting rapid access to densely functionalized bicyclic architectures.Keywords
Funding Information
- Erasmus+
- Ministerio de Ciencia, Innovación y Universidades (FPU22/01103)
- Ministerio de Ciencia, Innovación y Universidades (PID2024-158213NB-I00)
- Generalitat de Catalunya (2021SGR268)
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