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Asymmetric Allylic Alkylation of Morita-Baylis-Hillman Carbonates with α-Fluoro-β-Keto Esters
- TCHLab
- Sep 11, 2013
- 1 min read
Lin Yan, Zhiqiang Han, Bo Zhu, Caiyun Yang, Choon-Hong Tan and Zhiyong Jiang
Beilsten Journal of Organic Chemistry, 2013, 9, 1853 – 1857
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).
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