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  • Title: Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones.
    Author: Tong G, Zhu B, Lee R, Yang W, Tan D, Yang C, Han Z, Yan L, Huang KW, Jiang Z.
    Journal: J Org Chem; 2013 May 17; 78(10):5067-72. PubMed ID: 23594149.
    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.
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