Organic Chemistry Portal

Abstracts

Search:

Successive Nucleophilic and Electrophilic Allylation for the Catalytic Enantioselective Synthesis of 2,4-Disubstituted Pyrrolidines

Guoshun Luo, Ming Xiang, Michael J. Krische*

*Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States, Email: mkrischemail.utexas.edu

G. Luo, M. Xiang, M. J. Krische, Org. Lett., 2019, 21, 2493-2497.

DOI: 10.1021/acs.orglett.9b00508 (free Supporting Information)



see article for more reactions

Abstract

Successive nucleophilic and electrophilic allylation of a bis-Boc-carbonate derived from 2-methylene-1,3-propane diol provides enantiomerically enriched 2,4-disubstituted pyrrolidines. An initial enantioselective iridium-catalyzed transfer hydrogenative carbonyl C-allylation is followed by Tsuji-Trost N-allylation using 2-nitrobenzenesulfonamide and a Mitsunobu cyclization.

see article for more examples



Key Words

Pyrrolidines, Mitsunobu Reaction


ID: J54-Y2019