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Organocatalytic Enantioselective Allylic Etherification of Morita–Baylis–Hillman Carbonates and Silanols

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journal contribution
posted on 22.09.2016, 00:00 by Hui-Li Liu, Ming-Sheng Xie, Gui-Rong Qu, Hai-Ming Guo
The organocatalytic asymmetric allylic etherification reaction of Morita–Baylis–Hillman carbonates and silanols was reported for the first time. With modified cinchona alkaloid (DHQD)2PYR as the catalyst, a series of aromatic, heterocyclic, or aliphatic Morita–Baylis–Hillman carbonates (25 examples) worked well with triphenylsilanol, affording the corresponding products in moderate to good yields (up to 98%), high regioselectivities (>20:1), and good enantioselectivities (up to 92%). When dimethylphenylsilanol was used as the nucleophile, the product was obtained in 60% yield and 87% ee.