Diastereocontrol in the Synthesis of 2,3,4-Trisubstituted Pyrrolidines and Tetrahydrofurans via a Palladium(II)-Catalyzed Three-Component Coupling Reaction

Sandeep Raikar; Benoy Kumar Pal; Helena C. Malinakova

doi:10.1055/s-0031-1290969

Synthesis, Table of Contents

Synthesis 2012; 44(13): 1983-1992
DOI: 10.1055/s-0031-1290969

paper

Diastereocontrol in the Synthesis of 2,3,4-Trisubstituted Pyrrolidines and Tetrahydrofurans via a Palladium(II)-Catalyzed Three-Component Coupling Reaction

Authors

Sandeep Raikar

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA

Center of Excellence in Chemical Methodologies and Library Development, University of Kansas, 2034 Becker Drive, Shankel Structural Biology Center, West Campus, Lawrence, KS 66047, USA, Fax: +1(785)8645396 Email: hmalina@ku.edu
Benoy Kumar Pal

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA

Center of Excellence in Chemical Methodologies and Library Development, University of Kansas, 2034 Becker Drive, Shankel Structural Biology Center, West Campus, Lawrence, KS 66047, USA, Fax: +1(785)8645396 Email: hmalina@ku.edu
Helena C. Malinakova*

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA

Center of Excellence in Chemical Methodologies and Library Development, University of Kansas, 2034 Becker Drive, Shankel Structural Biology Center, West Campus, Lawrence, KS 66047, USA, Fax: +1(785)8645396 Email: hmalina@ku.edu

Abstract

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Abstract

The synthesis of trisubstituted pyrrolidines and tetrahydrofurans from boronic acids, allenes, and imines or aldehydes via a five- and a three-step protocol, respectively, is described. The assignment of the relative stereochemistry in the pyrrolidines and tetrahydrofurans confirmed the mechanistically significant stereochemical divergence of the palladium-catalyzed three-component coupling reaction. The methodology is applicable to the preparation of combinatorial libraries of pyrrolidines related to pharmaceutical agents and bioactive natural products.

Key words

stereoselective synthesis - heterocycles - palladium - multicomponent reactions - ring closure

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References

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