High-diastereoselective and enantioselective cyclopropanation of alpha,beta-unsaturated Fischer carbene complexes: Synthesis of chiral 1,2-disubstituted and 1,2,5-trisubstituted cyclopropanes

被引：36

作者：

Barluenga, J

Bernad, PL

Concellon, JM

PineraNicolas, A

GarciaGranda, S

机构：

[1] UNIV OVIEDO,INST UNIV QUIM ORGANOMET ENRIQUE MOLES,E-33071 OVIEDO,SPAIN

[2] UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 20期

关键词：

D O I：

10.1021/jo9708708

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of chiral vinylcarbene complexes 1 with in situ-generated iodomethyllithium or dibromomethyllithium gives cyclopropylcarbene complexes 4 and 13, respectively, with high diastereoselectivity (de > 91%). Different enantiopure 1,2-disubstituted and 1,2,3-trisubstituted cyclopropanes are obtained starting from chiral carbene complexes 4 and 13, respectively.

引用

页码：6870 / 6875

页数：6

共 63 条

[1] [Anonymous], ADV METAL ORGANIC CH
[2] Arndt F., 1943, ORG SYNTH, V2, P165
[3] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .2. 1-CHROMA-1,3-BUTADIENES AND 1-CHROMA-1,3,5-HEXATRIENES FROM (CO)5CR=C(OC2H5)CH3 BY CARBONYL OLEFINATION CATALYZED WITH TRIETHYLAMINE CHLOROTRIMETHYLSILANE
AUMANN, R
HEINEN, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (04): : 537 - 540
[4] AN EFFICIENT CONVERSION OF AROMATIC FISCHER CARBENE COMPLEXES INTO METHYLKETONES
BARLUENGA, J
BERNAD, PL
CONCELLON, JM
[J]. TETRAHEDRON LETTERS, 1994, 35 (50) : 9471 - 9472
[5] TOTAL DIASTEREOSELECTIVE SYNTHESIS OF CHROMIUM CYCLOPROPYLCARBENE COMPLEXES
BARLUENGA, J
BERNAD, PL
CONCELLON, JM
[J]. TETRAHEDRON LETTERS, 1995, 36 (22) : 3937 - 3940
[6] BARLUENGA J, 1994, ANGEW CHEM INT EDIT, V33, P1392, DOI 10.1002/anie.199413921
[7] ASYMMETRIC SYN-SELECTIVE MICHAEL ADDITION OF ENOLATES TO CHIRAL 8-PHENYLMENTHYLOXY VINYL CHROMIUM CARBENE COMPLEXES
BARLUENGA, J
MONTSERRAT, JM
FLOREZ, J
GARCIAGRANDA, S
MARTIN, E
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (04) : 236 - 242
[8] REACTION OF METAL-CARBENE COMPLEXES WITH WITTIG REAGENTS - NEW VINYL ETHER SYNTHESIS
CASEY, CP
BURKHARD.TJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (18) : 6543 - &
[9] CASEY CP, 1973, TETRAHEDRON LETT, P1421
[10] SYNTHESIS AND CRYSTAL-STRUCTURE OF DIPHENYLCARBENE(PENTACARBONYL)TUNGSTEN(0)
CASEY, CP
BURKHARDT, TJ
BUNNELL, CA
CALABRESE, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) : 2127 - 2134

← 1 2 3 4 5 6 7 →