Abstract
The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-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. © 2013 American Chemical Society.
Original language | English (US) |
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Pages (from-to) | 5067-5072 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 78 |
Issue number | 10 |
DOIs | |
State | Published - Apr 26 2013 |
ASJC Scopus subject areas
- Organic Chemistry
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Datasets
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CCDC 909467: Experimental Crystal Structure Determination : Methyl 2-methylene-3-phenyl-4-(2-thienylcarbonyl)hex-5-enoate
Tong, G. (Creator), Zhu, B. (Creator), Lee, R. (Creator), Yang, W. (Creator), Tan, D. (Creator), Yang, C. (Creator), Han, Z. (Creator), Yan, L. (Creator), Huang, K. (Creator) & Jiang, Z. (Creator), Dryad Digital Repository, 2013
DOI: 10.5517/cczjcnh, http://hdl.handle.net/10754/624757
Dataset