Stereocontrolled Synthesis of Highly Functionalized Quaternary Carbon Centers: A Route to α-Substituted Serines

被引：11

作者：

Ariza, Xavier ^{[1
]}

Cornella, Josep ^{[1
]}

Font-Bardia, Merce ^{[2
]}

Garcia, Jordi ^{[1
]}

Ortiz, Jordi ^{[1
]}

Sanchez, Carolina ^{[1
]}

Solans, Xavier ^{[2
]}

机构：

[1] Univ Barcelona, Fac Quim, Dept Quim Organ, IBUB, E-08028 Barcelona, Spain

[2] Univ Barcelona, Fac Geol, Dept Cristalog Mineral & Depositos Minerales, E-08028 Barcelona, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 23期

关键词：

allenes; amino alcohols; asymmetric synthesis; boranes; substituted serines; STEREOSELECTIVE-SYNTHESIS; AMINO-ACIDS; ACTIVE COMPOUNDS; ALDEHYDES; STEREOCENTERS; CONSTRUCTION; ALCOHOLS; KETONES; GLYCERALDEHYDE; REAGENTS;

D O I：

10.1002/anie.200900609

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Three in a row! Highly functionalized quaternary amino polyols with three consecutive asymmetric carbon centers have been prepared through tandem hydroboration of allene 1 and addition to an aldehyde (see scheme; Cy=cyclohexyl, TBDPS=tert-butyldiphenylsilyl, Ts=4-toluenesulfonyl). This one-pot process provides access to advanced intermediates for the enantioselective synthesis of α-substituted serines. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4202 / 4205

页数：4

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