Diastereodivergent synthesis of enantiomerically pure homoallylic amine derivatives containing quaternary carbon stereocenters

被引：56

作者：

Kolodney, Goren ^{[1
,2
]}

Sklute, Genia ^{[1
,2
]}

Perrone, Sylvie ^{[3
]}

Knochel, Paul ^{[3
]}

Marek, Ilan ^{[1
,2
]}

机构：

[1] Technion Israel Inst Technol, Mallat Family Lab Organ Chem, Schulich Fac Chem, IL-32000 Haifa, Israel

[2] Technion Israel Inst Technol, Lise Meitner Minerva Ctr Computat Quantum Chem, IL-32000 Haifa, Israel

[3] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 48期

关键词：

asymmetric synthesis; carbometalation; homoallylic amines; homologation; sulfinylimines;

D O I：

10.1002/anie.200702981

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Freedom of choice: Both enantiomers of free homoallylic amines with two stereogenic centers (including a quaternary center) can be prepared at will from vinyl copper intermediates derived from either a vinyl iodide or an alkyne (see examples; the sulfinyl group is cleaved readily under mild acidic conditions). In this one-pot strategy, zinc homologation of the vinyl copper species is followed by treatment with a sulfinylimine derivative. (Chemical Equation Presented) © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9291 / 9294

页数：4

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