Asymmetric Synthesis of 2,3,4-Trisubstituted Functionalised Tetrahydrofurans via an Organocatalytic Michael Addition as Key Step

作者：Enders Dieter^*; Wang Chuan; Greb Andreas

来源：Advanced Synthesis & Catalysis, 2010, 352(6): 987-992.

DOI：10.1002/adsc.200900879

• asymmetric synthesis
• Michael addition
• nitroalkenes
• organocatalysis
• tetrahydrofurans

The organocatalytic Michael addition of various aldehydes to (2E,4E)-ethyl 5-nitropenta-2,4dienoate has been achieved under the catalysis of diphenylprolinol trimethylsilyl ether furnishing the products in good to excellent yields (61-94%) and high stereoselectivities (dr up to >98:2, ee=97 to > 99%). Starting from these Michael adducts, 2,3,4trisubstituted functionalized tetrahydrofurans are available in two steps by reduction of the aldehyde followed by an intramolecular oxa-Michael addition in good yields (54-76%) and stereoselectivities (dr up to >95:5, ee= 97 to >99%).

• 出版日期2010-4