Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 40, Pages 10473-10485Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901577
Keywords
asymmetric catalysis; conjugate addition; copper; enones; P ligands
Categories
Funding
- Swiss National Research Foundation [200020-113332]
- COST action D40 [C07.0097]
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SimplePhos ligands represent a novel class of monodentate chiral ligands based on a chiral amine moiety and flexible diaryl groups on the phosphorous atom. They can be easily prepared by two different pathways and they can be highly functionalised. Herein we report the copper-catalysed asymmetric conjugate addition of diethyl zinc and trialkylaluminium reagents with SimplePhos ligands, which gives high enantioselectivity with cyclic enones, acyclic enones and nitro-olefins, with up to 98.6% ee. Of particular interest is the reaction of trialkylaluminium reagents with a wide range of 3-substituted enones, thus allowing the formation of stereogenic quaternary carbon centres.
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