Asymmetric Synthesis of Cyclic Alkenes via Cyclization of Enantioenriched Allylsilanes

Michinori Suginome; Taisuke Iwanami; Akihiko Yamamoto; Yoshihiko Ito

doi:10.1055/s-2001-14656

Synlett 2001; 2001(Special Issue): 1042-1045
DOI: 10.1055/s-2001-14656

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Asymmetric Synthesis of Cyclic Alkenes via Cyclization of Enantioenriched Allylsilanes

Michinori Suginome^* , Taisuke Iwanami, Akihiko Yamamoto, Yoshihiko Ito

^*Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan; Fax + 81(75)7 53 56 68; E-mail: suginome@sbchem.kyoto-u.ac.jp

Abstract

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Intramolecular cyclization of optically active allylsilanes bearing electrophilic functional groups on their α-alkyl side chains were examined. The allylsilanes having aldehyde and enone functional groups underwent the intramolecular cyclizations in the presence of Lewis acid catalysts to give 6- and 7-membered cycloalkenes with high stereoselectivity in good yields. Reactions of the allylsilanes having α-hydroxylalkyl chain with aldehydes provided 6- and 7-membered oxacycloalk-4-enes stereoselectively in good yields. Use of highly enantioenriched allylsilanes furnished enantioenriched cyclic alkenes with almost perfect chirality transfer from the allylsilanes.

allylations - chirality transfer - Lewis acids - silicon - stereoselective synthesis

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