Regio‐ and Enantioselective Organocascade Michael–Michael Reactions: Construction of Chiral Trisubstituted Indanes

Abstract

Given the importance of indane derivatives in both organic and medicinal chemistry, the development of an effective synthetic protocol for the preparation of multifunctionalized 1,2,3‐trisubstituted indane derivatives is of considerable interest. In this paper, we developed a cascade regio‐ and enantioselective double Michael addition to construct challenging multifunctionalized chiral indane derivatives in the presence of a bifunctional acid–base organocatalyst. The resulting optically active indane derivatives with three alternating trans stereocenters were produced in moderate to good yields with excellent diastereoselectivities and excellent enantioselectivities. Remarkably, the resulting products were facilely converted into multifunctionalized optically active (1‐indanylmethyl)amine and tetrahydroindeno[2,1‐b]pyrrole derivatives.

Recent Progress in Organocatalytic Asymmetric Domino Transformations

“…Wang and co‐workers devised a synthesis of chiral indane derivatives by using the strategy developed by Luo, and Xu, and co‐workers (Scheme ) . As shown in Scheme , ortho ‐functionalized aromatic dienones 577 was reacted with nitromethane ( 487 ) under the catalysis of the hydroquinidine‐derived thiourea catalyst 579 to produce the indane derivatives 578 in good to high yields and stereoselectivities . The enantiomers of 578 could be simply obtained in similar stereoselectivities by using the hydroquinine‐derived catalyst 489 (a pseudo‐enantiomer of 579 ) …”