Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins

Abstract

We report herein an enantioselective acyl transfer protocol via electrophile activation. The reaction cascade sequence encompasses dinuclear zinc-catalyzed asymmetric Michael addition, intramolecular cyclization, and retro-Claisen reaction, which leads to a step- and atom-economic approach to a variety of protected cyclic tertiary α-hydroxyketones in good yields with excellent enantioselectivities (24 examples, 56%-82% yield, 1.5-13 dr and 79%-96% ee). Besides, the large-scale synthesis and further transformation of the products demonstrate the effectiveness of this method for organic synthesis.

Reversal of enantioselectivity by tuning the ring size of ProPhenol

“…32–42 The excellent performance of this ligand also attracted our attention. 43–49 In 2014, we reported the ProPhenol analogue ( S , S )- L 4 as a new addition to the chiral aza-crown family by replacing the prolinol moieties with chiral azetidines (Fig. 1C).…”