A chiral auxiliary cleavable by ring-closing alkene metathesis - Efficient synthesis of chiral nonracemic cycloalkenes (Downloadable article, 2006) [WorldCat.org]
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A chiral auxiliary cleavable by ring-closing alkene metathesis - Efficient synthesis of chiral nonracemic cycloalkenes

Author: Luc Boisvert; Francis Beaumier; Claude Spino
Edition/Format: Downloadable article Downloadable article : English
Publication:Canadian Journal of Chemistry, v84 n10 (20061001) 1290-1293
Other Databases: WorldCatWorldCat
Summary:
p-Menthane-3-carboxaldehyde is a readily available chiral auxiliary used to prepare cycloalkenes and heterocycles bearing a chiral tertiary or quaternary carbon of high enantiomeric purity. The auxiliary is available in both enantiomeric forms and is inexpensive and recyclable. It is cleaved by a ring-closing alkene metathesis reaction directly yielding the cycloalkene.Key words: chiral auxiliary, cleavage reaction,  Read more...
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Details

Document Type: Article
All Authors / Contributors: Luc Boisvert; Francis Beaumier; Claude Spino
ISSN:0008-4042
Language Note: English
Unique Identifier: 5140506726
Awards:

Abstract:

p-Menthane-3-carboxaldehyde is a readily available chiral auxiliary used to prepare cycloalkenes and heterocycles bearing a chiral tertiary or quaternary carbon of high enantiomeric purity. The auxiliary is available in both enantiomeric forms and is inexpensive and recyclable. It is cleaved by a ring-closing alkene metathesis reaction directly yielding the cycloalkene.Key words: chiral auxiliary, cleavage reaction, cyclization, ring-closing alkene metathesis, enantioenriched cycloalkenes. Le p-menthane-3-carboxaldéhyde est utilisé comme auxiliaire chiral pour fabriquer des cycloalcènes et des hétérocycles contenant un centre carboné tertiaire ou quaternaire de pureté énantiomérique élevée. L'auxiliaire est disponible dans les deux séries énantiomériques et est peu dispendieux et recyclable. Il est clivé par une réaction de fermeture de cycle par métathèse d'alcènes menant directement au cycloalcène.Mots clés : auxiliaire chiral, réaction de clivage, cyclisation, fermeture de cycle par métathèse d'alcènes, cycloalcènes énantioenrichis.

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