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Synfacts 2009(10): 1133-1133  
DOI: 10.1055/s-0029-1217842
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of Functionalized Pyrrolizidinones

Contributor(s): Mark Lautens, Chit Tsui
L. Zoute, G. Kociok-Köhn, C. G. Frost*
University of Bath, UK
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Publikationsdatum:
22. September 2009 (online)

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Significance

Described here is a convenient stereoselective route to functionalized pyrrolizidinones using Rh-catalyzed 1,4-addition of arylboronic acids to an enantiopure acceptor 1 derived from (S)-prolinol. The protocol allows access to all four stereoisomers of pyrrolizidinone 3 (Ar = Ph) in high yields and excellent diastereoselectivities by appropriate choice of substrate and catalyst.