Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 6, Pages 987-992Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900879
Keywords
asymmetric synthesis; Michael addition; nitroalkenes; organocatalysis; tetrahydrofurans
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Funding
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
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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%).
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