Regio- and enantioselective carbolithiation of non-activated C=C bonds

被引：22

作者：

Norsikian, S ^{[1
]}

Baudry, M ^{[1
]}

Normant, JF ^{[1
]}

机构：

[1] Univ Paris 06, Associe CNRS, Lab Chim Organo Elements, F-75252 Paris 05, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 34期

关键词：

carbometalation; (-)-sparteine; enantioselection;

D O I：

10.1016/S0040-4039(00)01091-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Primary alkyllithiums in the presence of (-)-sparteine, add to terminal conjugated dienes. They also add to 2,4-pentadien-1-ols if they are substituted on C(5), and give rise to allyllithium intermediates, 2-Alkylalkan-1-ols have thus been prepared with ee's up to 74%. (C) 2000 Elsevier Science Ltd, All rights reserved.

引用

页码：6575 / 6578

页数：4

共 25 条

[1] CHIRAL DIAMINES FOR A NEW PROTOCOL TO DETERMINE THE ENANTIOMERIC COMPOSITION OF ALCOHOLS, THIOLS, AND AMINES BY P-31, H-1, C-13, AND F-19 NMR [J].

ALEXAKIS, A ;

FRUTOS, JC ;

MUTTI, S ;

MANGENEY, P .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3326-3334

[2] Z-trifluoromethyl thioenol ethers, enol ethers, and enamines; Reactivity towards organolithium reagents. [J].

Begue, JP ;

BonnetDelpon, D ;

Rock, MH .

TETRAHEDRON LETTERS, 1996, 37 (02) :171-174

[3] A SYNTHESIS OF (-)-TALAROMYCIN-A [J].

CRIMMINS, MT ;

OMAHONY, R .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1157-1161

[4] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[5]

EVERHARDUS RH, 1978, RECL TRAV CHIM PAY B, V97, P69

[6] UNEXPECTED BEHAVIOR OF DIENOL THIOETHERS GIVES VERSATILE ACCESS TO A LARGE SET OF FUNCTIONALIZED DIENES [J].

GAONACH, O ;

MADDALUNO, J ;

CHAUVIN, J ;

DUHAMEL, L .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :4045-4048

[7]

GLAZE WH, 1972, J ORGANOMET CHEM, V44, P49, DOI 10.1016/0022-328X(72)80041-X

[8] 3-NEOPENTYLALLYLLITHIUM .1. 1,4-ADDITION PRODUCT OF TERT-BUTYLLITHIUM AND 1,3-BUTADIENE [J].

GLAZE, WH ;

CHAUDHUR.J ;

HANICAK, JE ;

MOORE, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 44 (01) :39-&

[9] ALLYL-LITHIUM ADDUCTS FROM BUTA-1,3-DIENE AND S- OR T-BUTYL-LITHIUM [J].

GLAZE, WH ;

JONES, PC .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (23) :1434-&

[10] A VERSATILE AND STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES [J].

HEROLD, P ;

DUTHALER, R ;

RIHS, G ;

ANGST, C .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1178-1185

← 1 2 3 →