Enantioselective synthesis of spiropentanes from hydroxymethylallenes

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3293-3295

  Charette, André B ^a   Jolicoeur, Eric ^a   Bydlinski, Gregory A S ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL COENZYME A DESATURASE; ALKADIENE; ALLENE; ENZYME INHIBITOR; SPIRO COMPOUND; SPIROPENTANEACETIC ACID;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

ALKADIENES; ENZYME INHIBITORS; FATTY ACID DESATURASES; SPIRO COMPOUNDS;

EID: 0035909632     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0165140     Document Type: Article

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27. The absolute stereochemistry has been established only in the case of entry 7 for which an X-ray crystal structure of the (S)-Mosher ester derivative has been obtained (see Supporting Information for details).
28. When reaction was stopped after the addition of only one treatment of zinc reagent. A lower yield and ee was observed (25% yield, 83% ee).
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31. Unoptimized yield.
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34. Application of the methodology to a homoallenic alcohol (3,4-butadiene-1-ol) provided the desired spiropentane with only 47% ee.