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J Org Chem. 2008 Nov 7;73(21):8133-41. doi: 10.1021/jo801503c. Epub 2008 Sep 23.

Traceless chiral auxiliaries for the allene ether Nazarov cyclization.

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  • 1University of Hawaii, Chemistry Department, Honolulu, Hawaii 96822, USA.

Abstract

The key stereochemical factors that determine transfer of asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazarov reaction have been elucidated. On the basis of the new insights into the mechanism, two highly effective chiral auxiliaries were designed and prepared.

PMID:
18808186
PMCID:
PMC2674073
DOI:
10.1021/jo801503c
[PubMed - indexed for MEDLINE]
Free PMC Article
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