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Synlett 1999; 1999(S1): 972-974
DOI: 10.1055/s-1999-3099
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Enantioselective Synthesis of Alkyl-substituted Eight-membered Lactones by Claisen Rearrangement

Justin R. Harrison* , Andrew B. Holmes, Ian Collins
  • *University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK; Fax +44(12 23)33 63 62; E-mail: abh1@cus.cam.ac.uk
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Publication History

Publication Date:
31 December 1999 (online)

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The Claisen rearrangement of alkenyl-substituted ketene acetals (produced in situ by selenoxide elimination from the corresponding phenylselenoacetaldehyde-derived acetals of enantiomerically pure 1,3-diol derivatives) afforded unsaturated eight-membered lactones with control of stereochemistry of methyl substituents at C-4, C-5 and C-7, as well as a fused system.

[3.3]-sigmatropic - lactone - aldol - boron - enantioselective