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Phosphine-Catalyzed (3 + 2) Annulation of γ-Substituted Cinnamic Aldehyde-Derived Morita-Baylis-Hillman Carbonates
Yue Ren1, Wangyu Shi1, Yi Tang1
1Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, Beijing 100193, P. R. China.
Abstract:
A series of γ-substituted Morita-Baylis-Hillman (MBH) carbonates were synthesized and subjected to phosphine-catalyzed annulations with electrophilic exocyclic alkenes, giving various valuable spirocyclopentenes in moderate to excellent yields with moderate to excellent diastereoselectivities. A large scope of MBH carbonates bearing γ-hydrogen, alkenyl, and alkynyl substituents was well tolerated. The annulation unprecedentedly involves β-, γ-, and δ-carbons of MBH carbonates.
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