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Paper | Special issue | Vol 95, No. 2, 2017, pp.872-893
Published online, 5th December, 2016
DOI: 10.3987/COM-16-S(S)56
Catalytic and Enantioselective Diels-Alder Reaction of Silyloxydiene That Incorporates a Pyrrolidine Ring, and Its Application to the Construction of Chiral Tri- and Tetracyclic Skeletons

Shinji Harada, Saki Nakashima, Wataru Yamada, Takahiro Morikawa, and Atsushi Nishida*

*Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, Japan

Abstract

The enantioselective Diels-Alder reaction of silyloxydiene that incorporates a pyrrolidine ring was studied. This reaction was catalyzed by a chiral holmium complex and gave multi-substituted chiral hydroindoles that contained a silyl enol ether, which is a key functional group for further transformations. We demonstrate here the synthesis of chiral pyrroloacridine, dibenzodiazocine, and pyrrolocarbazole skeletons.