Catalytic enantioselective Diels-Alder reactions using titanium complexes of cis-N-sulfonyl-2-amino-1-indanols

Abstract

A titanium complex derived from (1R, 2S)-N-(2,4,6-trimethylbenzenesulfonyl)-2-amino-1-indanol catalyzes the Diels-Alder reaction of 2-bromoacrolein and cyclopentadiene with 96.5:3.5 enantioselectivity. A new and efficient synthesis of 2-amino-1-indanol (6) contributes to the potential of this methodology. © 1993.