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Synfacts 2006(1): 0045-0045  
DOI: 10.1055/s-2005-921739
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

1,2-Disubstituted Cyclopentanes by Catalyzed C-H Insertion Reactions of α-Diazo Esters

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
K. Minami, H. Saito, H. Tsutsui, H. Nambu, M. Anada, S. Hashimoto*
Hokkaido University, Japan
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Publikationsdatum:
16. Dezember 2005 (online)

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Significance

A highly diastereo- and enantioselective C-H insertion reaction of α-diazo esters with no evidence of alkene formation (β-hydride elimination) is reported. High cis-selectivity is shown for C-H insertion to the benzylic position of a variety of compounds (subtitution on the benzene ring). High trans-selectivity was shown for the compound possessing a n-butyl group next to the insertion site.