Literature DB >> 15917897

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

Kristin M Brinner1, Jonathan A Ellman.   

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.

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Year:  2005        PMID： 15917897     DOI： 10.1039/b502080h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  11 in total

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7.  Total synthesis of stemaphylline N-oxide and related C9a-epimeric analogues.

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Journal:  Chemistry       Date:  2013-08-16       Impact factor: 5.236

8.  Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles.

Authors:  Joanne E Redford; Richard I McDonald; Matthew L Rigsby; Joshua D Wiensch; Shannon S Stahl
Journal:  Org Lett       Date:  2012-02-21       Impact factor: 6.005

9.  3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.

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Journal:  Tetrahedron Lett       Date:  2013-03-27       Impact factor: 2.415
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