Morita-Baylis-Hillman 碳酸酯与 α-氟代-β-酮酯的不对称烯丙基烷基化反应。
Asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with α-fluoro-β-keto esters.
机构信息
Institute of Chemical Biology, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P. R. China.
出版信息
Beilstein J Org Chem. 2013 Sep 11;9:1853-7. doi: 10.3762/bjoc.9.216. eCollection 2013.
Abstract
In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).
摘要
在市售金鸡纳生物碱催化剂的存在下，成功开发了 Morita-Baylis-Hillman 碳酸酯与α-氟代-β-酮酯作为亲核试剂的不对称烯丙基烷基化反应。以良好的收率（高达 93%）、良好到优秀的对映选择性（高达 96%ee）和中等的非对映选择性（高达 4:1dr）获得了一系列重要的含氟加成产物，产物具有手性季碳原子和氟原子。
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