Issue 12, 2023

Progress in catalytic asymmetric α-functionalization of vinylogous nucleophilic species

Abstract

In conjugated π systems, π-extended enolates generated in situ from unsaturated pronucleophiles through suitable HOMO-raising strategies tend to proceed via stereoselective vinylogous reactions that sterically favored remote functionalization (γ-, ε-, and ω-positions of the carbonyl group). In contrast, proximal functionalization (α-position) of bench-stable unsaturated pronucleophiles has historically remained underdeveloped or has not existed. To counter these obstacles, new synthetic methods and efficient catalytic systems have been developed in the last few years. This review focuses on the recent exciting achievements in the proximal functionalization of unsaturated pronucleophiles, such as unsaturated aldehydes, ketones, carboxylic acids, and their derivatives and analogs. Mechanistic insights, transition states, and some synthetic applications are summarized. The challenges and opportunities of this field are also discussed.

Graphical abstract: Progress in catalytic asymmetric α-functionalization of vinylogous nucleophilic species

Article information

Article type
Review Article
Submitted
05 4 2023
Accepted
02 5 2023
First published
02 5 2023

Org. Chem. Front., 2023,10, 3130-3168

Progress in catalytic asymmetric α-functionalization of vinylogous nucleophilic species

Z. Wang, Y. You, J. Zhao, Y. Zhang, J. Yin and W. Yuan, Org. Chem. Front., 2023, 10, 3130 DOI: 10.1039/D3QO00506B

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