Metalated 2-Alkenylsulfoximides in Asymmetric Synthesis: Diastereoselective Preparation of Highly Substituted Pyrrolidine Derivatives

Michael Reggelin; Timo Heinrich

doi:10.1002/(SICI)1521-3773(19981102)37:20<2883::AID-ANIE2883>3.0.CO;2-Y

Metalated 2-Alkenylsulfoximides in Asymmetric Synthesis: Diastereoselective Preparation of Highly Substituted Pyrrolidine Derivatives

Angew Chem Int Ed Engl. 1998 Nov 2;37(20):2883-2886. doi: 10.1002/(SICI)1521-3773(19981102)37:20<2883::AID-ANIE2883>3.0.CO;2-Y.

Authors

Michael Reggelin¹, Timo Heinrich¹

Affiliation

¹ Fachbereich Chemie der Universität, Marie-Curie-Strasse 11, D-60439 Frankfurt/Main (Germany), Fax: (+49) 69-7982-9128.

Abstract

Thanks to a productive interaction between reagent and substrate control, 2-alkenylsulfoximides 1 react to provide highly substituted pyrrolidine derivatives 2 enantiomerically pure and with defined absolute configuration at the newly formed stereogenic centers. Tol=tolyl, BOC=tert-butoxycarbonyl.

Keywords: Asymmetric synthesis; Heterocycles; Pyrrolidines; Samarium; Sulfoximines.