Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue -, Pages 1098-1104Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.8.121
Keywords
asymmetric [3+2] annulation; maleimides; Morita-Baylis-Hillman carbonates; multifunctional thiourea-phosphine; organocatalysis
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Funding
- Shanghai Municipal Committee of Science and Technology [11JC1402600]
- National Basic Research Program of China (973) [2010CB833302]
- National Natural Science Foundation of China [21072206, 20472096, 20872162, 20672127, 21121062, 20732008]
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We have developed a multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with maleimides, which can efficiently construct functionalized cyclopentenes bearing three contiguous stereocenters in moderate to excellent yields and excellent diastereo- and enantioselectivities. A plausible mechanism has been also proposed on the basis of control experiments and previous literature.
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