Facile Synthesis of cis-2-Alkyl-3-trialkylsilyloxycycloalkanones via the Non-Aldol Aldol Rearrangement of 2,3-Epoxycycloalkanols

Silyl triflate-promoted rearrangement of cis-2,3-epoxycycloalkanols A, prepared by epoxidation of the cyclic allylic alcohol and then silylation, afforded good yields (∼70–75%) of the cis-2-alkyl-3-silyloxycycloalkanones B, presumably via the intermediates C and D, even with quite large α-substituen...

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Bibliographic Details
Published in:Organic letters 2008-05, Vol.10 (10), p.2039-2041
Main Authors: Jung, Michael E, Allen, Damian A
Format: Article
Language:English
Subjects:
Epoxy Compounds - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Conformation
Silanes - chemical synthesis
Silanes - chemistry
Stereoisomerism
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Summary:Silyl triflate-promoted rearrangement of cis-2,3-epoxycycloalkanols A, prepared by epoxidation of the cyclic allylic alcohol and then silylation, afforded good yields (∼70–75%) of the cis-2-alkyl-3-silyloxycycloalkanones B, presumably via the intermediates C and D, even with quite large α-substituents, e.g., tert-butyl. Finally, it has been shown that the stereochemistry of the epoxy alcohol is crucial as one would expect from the mechanism.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800423m