Issue 11, 2005
From the journal:

Organic & Biomolecular Chemistry

A rapid and general method for the asymmetric synthesis of 2-substituted pyrrolidines using tert-butanesulfinamide

Kristin M. Brinner†a  and  Jonathan A. Ellman*a  

* Corresponding authors

a Center for New Directions in Organic Synthesis, Chemistry Department, University of California, Berkeley, USA
E-mail: kristin_brinner@chiron.com, ellman@cchem.berkeley.edu
Fax: +1 510 642 8369
Tel: +1 510 642 4488

Abstract

A new method for the asymmetric synthesis of 2-substituted pyrrolidines in three steps from commercially available starting materials is described. Addition of the Grignard reagent prepared from 2-(2-bromoethyl)-1,3-dioxane to N-tert-butanesulfinyl aldimines proceeds in high yields and with good diastereoselectivities. The sulfinamide products are then cleanly converted into pyrrolidines in one step.

Graphical abstract: A rapid and general method for the asymmetric synthesis of 2-substituted pyrrolidines using tert-butanesulfinamide

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Article information

DOI
https://doi.org/10.1039/B502080H
Article type
Paper
Submitted
08 Mar 2005
Accepted
11 Apr 2005
First published
04 May 2005

Org. Biomol. Chem., 2005,3, 2109-2113

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A rapid and general method for the asymmetric synthesis of 2-substituted pyrrolidines using tert-butanesulfinamide

K. M. Brinner and J. A. Ellman, Org. Biomol. Chem., 2005, 3, 2109 DOI: 10.1039/B502080H

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