Asymmetric Synthesis of Cyclic Alkenes via Cyclization of Enantioenriched Allylsilanes

Intramolecular cyclizations of optically active allylsilanes bearing electrophilic functional groups on their alpha -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...

Full description

Saved in:
Bibliographic Details
Published inSynlett Vol. 2001; no. Special Issue; pp. 1042 - 1045
Main Authors Suginome, Michinori, Iwanami, Taisuke, Yamamoto, Akihiko, Ito, Yoshihiko
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2001
Subjects
Chemistry
Chemistry, Organic
letter
Physical Sciences
Science & Technology
Lewis acids
allylations
silicon
chirality transfer
stereoselective synthesis
OPTICALLY-ACTIVE ALLYLSILANES
MEDIATED CARBOCYCLIZATION
ALDEHYDES
INTRAMOLECULAR BIS-SILYLATION
Online AccessGet full text

Cover

More Information
Summary:Intramolecular cyclizations of optically active allylsilanes bearing electrophilic functional groups on their alpha -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 a-hydroxyalkyl 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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2001-14656