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

Hui-Li Liu, Ming-Sheng Xie, Gui-Rong Qu, Hai-Ming Guo

J Org Chem. 2016 Oct 21;81(20):10035-10042.

PMID: 27657512

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP5272184 Dimethylphenylsilanol Dimethylphenylsilanol 5272-18-4 Price
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