Chiral bidentate lithium amides having a chiral amide nitrogen for enantioselective deprotonation of 4-tert-butylcycloxexanone

被引：0

作者：

Chatani, H ^{[1
]}

Nakajima, M ^{[1
]}

Kawasaki, K ^{[1
]}

Koga, K ^{[1
]}

机构：

[1] Univ Tokyo, Fac Pharmaceut Sci, Bunkyo Ku, Tokyo 113, Japan

来源：

HETEROCYCLES | 1997年 / 46卷

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective deprotonation of 4-tert-butylcyclohexanone (1) by chiral bidentate lithium amides ((R)-5a similar to b) was examined in the presence of excess TMSCl in several solvents containing 2 equivalents of HMPA. The sense of asymmetric induction was found to be the same with that by using (R)-2a similar to b. This result suggests the formation of a similar chiral amide nitrogen in these chiral lithium amides.

引用

页码：53 / 56

页数：4

共 50 条

[31] Asymmetric synthesis of planar chiral (Arene) tricarbonylchromium complexes via enantioselective deprotonation by conformationally constrained chiral lithium-amide bases
Pache, S
Botuha, C
Franz, R
Kündig, EP
Einhorn, J
HELVETICA CHIMICA ACTA, 2000, 83 (09) : 2436 - 2451
[32] Enantioselective reduction of α,β-unsaturated acylsilanes by chiral lithium amides
Takeda, K
Ohnishi, Y
Koizumi, T
ORGANIC LETTERS, 1999, 1 (02) : 237 - 239
[33] ENANTIOSELECTIVE DEPROTONATION BY CHIRAL LITHIUM AMIDE BASES - ASYMMETRIC-SYNTHESIS OF TRIMETHYLSILYL ENOL ETHERS FROM 4-ALKYLCYCLOHEXANONES
SHIRAI, R
TANAKA, M
KOGA, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) : 543 - 545
[34] Chiral lithium amides on polymer support - Synthesis and use in deprotonation of ketones
Majewski, M
Ulaczyk-Lesanko, A
Wang, F
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2006, 84 (02): : 257 - 268
[35] CRYSTALLOGRAPHIC AND LI-6 AND N-15 NMR-STUDIES OF A CHIRAL BIDENTATE LITHIUM AMIDE - AN EFFECT OF AGGREGATION STATES ON AN ENANTIOSELECTIVE DEPROTONATION REACTION
SATO, D
KAWASAKI, H
SHIMADA, I
ARATA, Y
OKAMURA, K
DATE, T
KOGA, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) : 761 - 763
[36] Crystallographic and 6Li and 15N NMR studies of a chiral bidentate lithium amide. An effect of aggregation states on an enantioselective deprotonation reaction
1600, (114):
[37] ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES
CAIN, CM
COUSINS, RPC
COUMBARIDES, G
SIMPKINS, NS
TETRAHEDRON, 1990, 46 (02) : 523 - 544
[38] Stereoselective diamine chelates of a chiral lithium amide dimer: New insights into the coordination chemistry of chiral lithium amides
Arvidsson, PI
Hilmersson, G
Ahlberg, P
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) : 1883 - 1887
[39] ENANTIOSELECTIVE CARBOXYLATION OF A PROCHIRAL ENOLATE IN THE PRESENCE OF A CHIRAL LITHIUM AMIDE
HOGEVEEN, H
MENGE, WMPB
TETRAHEDRON LETTERS, 1986, 27 (24) : 2767 - 2770
[40] ENANTIOSELECTIVE ALDOL REACTION MEDIATED BY CHIRAL LITHIUM AMIDE BASES
MURAOKA, M
KAWASAKI, H
KOGA, K
TETRAHEDRON LETTERS, 1988, 29 (03) : 337 - 338

← 1 2 3 4 5 →