Solid-state structure and enantioselective reactions of a complex of a 1-thio-substituted propargyllithium and (-)-sparteine

被引：18

作者：

Otte, R ^{[1
]}

Fröhlich, R ^{[1
]}

Wibbeling, B ^{[1
]}

Hoppe, D ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 34期

关键词：

allenes; asymmetric synthesis; carbanions; lithiation; sparteine;

D O I：

10.1002/anie.200501142

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A useful transformation in enantioselective synthesis: (-)-Sparteine-assisted lithiation of the propargylic 1-thiocarbamate 1 (Cb = CONiPr2) forms the enantiomerically and diastereomerically pure lithium (-)-sparteine complex 2. Its solid-state structure and application in the asymmetric synthesis of highly enantioenriched 1-thioallenes 3 were investigated. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5492 / 5496

页数：5

共 50 条

[1] 1-THIO-SUBSTITUTED CYCLOPROPYLPHOSPHONIUM SALTS - REAGENTS FOR PENTANNULATION REACTIONS
MARINO, JP
FERRO, MP
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09): : 1828 - 1832
[2] Synthesis and solid-state structure of substituted arylphosphine oxides
J Org Chem, 11 (3499):
[3] SYNTHESIS AND SOLID-STATE STRUCTURE OF SUBSTITUTED ARYLPHOSPHINE OXIDES
WHITAKER, CM
KOTT, KL
MCMAHON, RJ
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11): : 3499 - 3508
[4] Synthesis and solid-state structure of a metal complex of a diphosphineimine
Anagho, LE
Bickley, JF
Steiner, A
Stahl, L
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (21) : 3271 - 3275
[5] REACTIONS IN THE SOLID-STATE .4. ENANTIOSELECTIVE PHOTOCHEMICAL-REACTIONS IN CRYSTALLINE INCLUSION-COMPOUNDS
KAFTORY, M
YAGI, M
TANAKA, K
TODA, F
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18): : 4391 - 4393
[6] STRUCTURE, EXTENDED DEFECTS, AND MECHANISMS IN INORGANIC SOLID-STATE REACTIONS
EYRING, L
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1980, 179 (MAR): : 106 - PHYS
[7] PHOTODIMERIZATION OF 1-SUBSTITUTED ACENAPHTHYLENES IN SOLUTION AND IN SOLID-STATE
BOUASLAURENT, H
CASTELLA.A
COURSEIL.C
HAUW, C
DUMARTIN, G
DESVERGN.JP
GAULTIER, J
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (23) : 1267 - +
[8] Structure and Segmental Motions in a Substituted Polythiophene: A Solid-State NMR Study
Le Bouch, Nolwenn
Auger, Michele
Leclerc, Mario
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2008, 209 (24) : 2455 - 2462
[9] A (-)-sparteine-directed highly enantioselective synthesis of boroproline.: Solid- and solution-state structure and properties
Batsanov, Andrei S.
Grosjean, Christophe
Schuetz, Thorben
Whiting, Andrew
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16): : 6276 - 6279
[10] LINEAR-FREE ENERGY RELATIONSHIPS IN SOLID-STATE REACTIONS .1. REACTIONS OF COBALT ACETATE WITH SUBSTITUTED ANILINE HYDROCHLORIDES
BASSI, PS
CHOPRA, GS
JOURNAL OF SOLID STATE CHEMISTRY, 1986, 61 (01) : 103 - 108

← 1 2 3 4 5 →