Palladium-catalyzed enantioselective decarboxylative cycloaddition of vinylethylene carbonates with isocyanates.
An efficient method for the enantioselective construction of β-substituted β-vinylglycinol derivatives through palladium-catalyzed decarboxylative cycloaddition of vinylethylene carbonates with isocyanates was developed. By using a palladium complex generated in situ from [Pd2 (dba)3]⋅CHCl3 (dba=dibenzylideneacetone) and (S)-Segphos as a catalyst under mild reaction conditions, the process provided 4-substituted-4-vinyloxazolidin-2-ones in high yields with a high level of enantioselectivity. The stereochemical outcome of the reaction was explained by DFT calculations and the synthetic utility of the process was demonstrated by the gram-scale transformation and formal synthesis of MK-0731 as a kinesin spindle protein inhibitor.
School of Chemistry and Chemical Engineering and Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P. R. China), Fax: (+86) 21-5474-1297.
Ajmal
A
Khan
Juxiang
J
Xing
Jingming
J
Zhao
Yuhe
Y
Kan
Wanbin
W
Zhang
Yong Jian
YJ
Zhang
amino alcohols; asymmetric catalysis; cycloaddition; palladium; substituted vinylglycinols