Asymmetric synthesis of functionalised cyclopentenones via organocatalysed rearrangement and enzymatic resolution of pyranones

A direct asymmetric synthesis of a trans-4,5-dioxygenated cyclopentenone derivative has been achieved by organocatalysed rearrangement of a pyranone in tert-butanol by DABCO and in situ enzymatic resolution A direct asymmetric synthesis of a trans-4,5-difunctionalised cyclopentenone derivative has b...

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Bibliographic Details
Published in:Tetrahedron letters 2009-07, Vol.50 (26), p.3706-3708
Main Authors: Nunes, João P.M., Afonso, Carlos A.M., Caddick, Stephen
Format: Article
Language:English
Subjects:
Chiral cyclopentenone
Enzymatic resolution
Isomerisation
Organocatalysis
Pyranone
Rearrangement
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Summary:A direct asymmetric synthesis of a trans-4,5-dioxygenated cyclopentenone derivative has been achieved by organocatalysed rearrangement of a pyranone in tert-butanol by DABCO and in situ enzymatic resolution A direct asymmetric synthesis of a trans-4,5-difunctionalised cyclopentenone derivative has been achieved in 55% yield and 80% ee by organocatalysed rearrangement of a pyranone in tert-butanol by DABCO with simultaneous enzymatic resolution.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.03.212