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Synfacts 2007(1): 0065-0065  
DOI: 10.1055/s-2006-955719
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

[3+2] Annulation of N-Ts-α-Amino Aldehydes and 1,3-Bis(silyl)propenes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
P. Restorp, A. Fischer, P. Somfai*
KTH Chemical Science and Engineering, Stockholm, Sweden
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

The authors describe a stereoselective synthesis of pyrrolidines via a [3+2] annulation with 1,3-bis(silyl)propenes. A number of silyl groups were tested and the Me2PhSi group was used due to its success as well as its ability to be oxidized under Tamao-Fleming conditions. Of the many Lewis acids tested, aluminium-based acids proved to be the best, with MeAlCl2 giving optimal results. A number of chiral aldehydes were used and all reactions proceeded with perfect diastereo­selectivity.