Organocatalytic Enantioselective Reaction of Cyclopent‐2‐enone‐Derived Morita–Baylis–Hillman Alcohols with 4‐Hydroxycoumarins

• DOI: 10.1002/adsc.201500443
• Publication Date: 2016-01-05T14:46:28Z
• Authors: Chuanli Ren; Feng Wei; Qingqing Xuan; Dong Wang; Li Liu
• Keywords: 01 natural sciences; 0104 chemical sciences

AbstractA direct enantioselective reaction of cyclopent‐2‐enone‐derived Morita–Baylis–Hillman alcohols with 4‐hydroxycoumarins has been developed under the catalysis of a chiral primary amine derived from cinchonine in combination with a Brønsted acid. The reaction provides pyranocoumarin products with three vicinal chiral carbon centers in highly regio‐, diastereo‐ and enantioselectivities through a tandem allylic alkylation/intramolecular oxa‐Michael addition.magnified image