Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 10, Pages 5067-5072Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400496z
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Funding
- National Natural Science Foundation of China [21072044, 21202034]
- Program for New Century Excellent Talents in University of Ministry of Education [NCET-11-0938]
- Excellent Youth Foundation of Henan Scientific Committee [114100510003]
- Specialized Research Fund for the Doctoral Program of Higher Education [20104103120002]
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The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The alpha-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared.
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