4.7 Article

Enatioselective Synthesis of Highly Functionalized Trifluoromethyl-Bearing Cyclopentenes: Asymmetric [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Trifluoroethylidenemalonates Catalyzed by Multifunctional Thiourea-Phosphines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 5, Pages 783-789

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201101012

Keywords

asymmetric [3+2]?annulation; Morita-Baylis-Hillman carbonates; multifunctional thiourea-phosphines; trifluoroethylidenemalonates; trifluoromethyl-bearing cyclopentenes

Funding

  1. National Basic Research Program of China (973) [2010CB833302]
  2. National Natural Science Foundation of China [21072206, 20472096, 20872162, 20672127, 20821002, 20732008]

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On the basis of the design and synthesis of multifunctional thiourea-phosphines, a catalytic method for the asymmetric [3+2]?annulation of MoritaBaylisHillman carbonates with trifluoroethylidenemalonates has been developed, affording highly functionalized trifluoromethyl-bearing cyclopentenes in excellent yields, high diastereoselectivities and enantioselectivities under mild conditions.

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