ENANTIOSELECTIVE SYNTHESIS VIA SPARTEINE-INDUCED ASYMMETRIC DEPROTONATION

被引：107

作者：

HOPPE, D ^{[1
]}

HINTZE, F ^{[1
]}

TEBBEN, P ^{[1
]}

PAETOW, M ^{[1
]}

AHRENS, H ^{[1
]}

SCHWERDTFEGER, J ^{[1
]}

SOMMERFELD, P ^{[1
]}

HALLER, J ^{[1
]}

GUARNIERI, W ^{[1
]}

KOLCZEWSKI, S ^{[1
]}

HENSE, T ^{[1
]}

HOPPE, I ^{[1
]}

机构：

[1] CHRISTIAN ALBRECHTS UNIV KIEL,DEPT ORGAN CHEM,W-2300 KIEL 1,GERMANY

来源：

PURE AND APPLIED CHEMISTRY | 1994年 / 66卷 / 07期

关键词：

D O I：

10.1351/pac199466071479

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The deprotonation of achiral alkyl carbamates with sec-butyllithium/(-)-sparteine proceeds with a high degree of chiral recognition to form substituted alcohols usually with greater-than-or-equal-to 95 % ee after reaction with electrophiles followed by deprotection. The stereoselection is kinetically controlled and a qualitative transition state model is proposed. Some studies, concerning the discrimination between both enantiomers of stereogenic alkyl carbamates and on its utilization for the kinetic resolution are reported. The competition between external and internal competition was investigated in few cases. - Finally, we disclose a short report on the enantioselective electrophilic substitution of 1-methylindene; here the origin of stereoselection is an thermodynamically driven epimerization of diastereomeric indenyl-lithium sparteine complexes.

引用

页码：1479 / 1486

页数：8

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