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

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.