Journal
TETRAHEDRON
Volume 67, Issue 24, Pages 4371-4377Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.03.071
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- Centre National de la Recherche Scientifique
- Ministere de l'Education et de la Recherche
- National Research Agency [ANR-09-JCJC-0078]
- Agence Nationale de la Recherche (ANR) [ANR-09-JCJC-0078] Funding Source: Agence Nationale de la Recherche (ANR)
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An efficient Au(I) catalytic system is described for the asymmetric domino cyclization/functionalization reactions of functionalized 1,6-enynes in the presence of an external nucleophile. The use of (R)-4-MeO-3,5-(t-Bu)(2)-MeOBIHEP ligand associated with gold led to clean rearrangements implying the formal addition of an oxygen or carbon nucleophile to an alkene followed by a cyclization process. The enantiomeric excesses were highly dependant on the substrate/nucleophile combination. Very good enantiomeric excesses up to 98% were obtained in the case of substrates bearing larger groups (hindered diesters and disulfones) and in the case of hindered carbon nucleophiles. (C) 2011 Elsevier Ltd. All rights reserved.
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