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Radical Migration-Addition of N-tert-Butanesulfinyl Imines with Organozinc Reagents 期刊论文

编号：

92ba174d-b18b-45e7-a416-f0a022b94f0b
作者：

Huang, Wei^[1,2] Ye, JianLiang^[3,4] Zheng, Wei^[1,2] Dong, HanQing^[5] Wei, BangGuo^[1,2]
语种：

英文
期刊：

JOURNAL OF ORGANIC CHEMISTRY ISSN：0022-3263 2013 年 78 卷 22 期 (11229 - 11237) ; NOV 15
收录：
摘要：

A novel migration-addition sequence was discovered for the reaction of enantioenriched N-tert-butanesulfinyl with iminoacetate la functionalized benzylzinc bromide reagents, producing tert-leucine derivatives in excellent diastereoselectivity (dr 98:2). The absolute configurations of two new chiral centers were unambiguously assigned by chemical transformations and X-ray crystallography. In addition, the regio- and diastereoselectivities of this novel reaction were both explained through the key N-sulfinamine intermediate M6 generated by the tert-butyl radical attack on the imine. Computational analysis of this reaction process, which was performed at the B3LYP/6-311++G(3df,2p)//B3LYP/6-31G*-LANL2DZ level, also supported our proposed two-stage mechanism.
推荐引用方式
GB/T 7714：

Huang Wei,Ye Jian-Liang,Zheng Wei, et al. Radical Migration-Addition of N-tert-Butanesulfinyl Imines with Organozinc Reagents [J].JOURNAL OF ORGANIC CHEMISTRY,2013,78(22):11229-11237.
APA：

Huang Wei,Ye Jian-Liang,Zheng Wei,Dong Han-Qing,&Wei Bang-Guo.(2013).Radical Migration-Addition of N-tert-Butanesulfinyl Imines with Organozinc Reagents .JOURNAL OF ORGANIC CHEMISTRY,78(22):11229-11237.
MLA：

Huang Wei, et al. "Radical Migration-Addition of N-tert-Butanesulfinyl Imines with Organozinc Reagents" .JOURNAL OF ORGANIC CHEMISTRY 78,22(2013):11229-11237.

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