期刊
ACS CATALYSIS
卷 1, 期 11, 页码 1637-1642出版社
AMER CHEMICAL SOC
DOI: 10.1021/cs200511z
关键词
hydroamination; enantioselectivity; pyrrolidine; rare-earth; organometallics; mechanism
资金
- U.S. Department of Energy, Office of Basic Energy Sciences, Division of Chemical Sciences, Geosciences, and Biosciences through the Ames Laboratory [DE-AC02-07CH11358]
- U.S. DOE Office of Science through the Science Undergraduate Laboratory
A highly active oxazolinylborato yttrium hydroamination catalyst provides 2-methyl-pyrrolidines with excellent optical purities. The proposed mechanism, in which a yttrium(amidoalkene)amine complex reacts by concerted C-N and C-H bond formation, is supported by the rate law for conversion, substrate saturation under initial rates conditions, kinetic isotope effects, and isotopic perturbation of enantioselectivity. These features are conserved between oxazolinylborato Mg-, Y-, and Zr-mediated aminoalkene cyclizations, suggesting related transition states for all three systems. However, inversion of the products' absolute configuration between yttrium and zirconium catalysts coordinated by the same 4S-oxazolinylborate ligands highlight dissimilar mechanisms of stereoinduction.
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