Highly diastereoselective Pauson-Khand reactions of a stable, internally chelated, dicobalt pentacarbonyl complex of a chiral acetylene thioether

被引：44

作者：

Montenegro, E ^{[1
]}

Poch, M ^{[1
]}

Moyano, A ^{[1
]}

Pericàs, MA ^{[1
]}

Riera, A ^{[1
]}

机构：

[1] Univ Barcelona, Fac Quim, Dept Quim Organ, Unitat Rec Sintesi Asimetr, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 3-4期

关键词：

D O I：

10.1016/S0040-4039(97)10482-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hexacarbonyl dicobalt complex of the acetylene thioether derived from (2R)exo-10-(methylthio)-2-bornanethiol has been prepared in good yield. This compound affords a stable internally chelated pentacarbonyl complex either by thermal or oxidative decarbonylation. Optimal conditions for the highly diastereoselective reaction of the chelated species have been developed. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：335 / 338

页数：4

共 30 条

[1] PRACTICAL ASYMMETRIC VERSION OF THE INTERMOLECULAR PAUSON-KHAND REACTION
BERNARDES, V
VERDAGUER, X
KARDOS, N
RIERA, A
MOYANO, A
PERICAS, MA
GREENE, AE
[J]. TETRAHEDRON LETTERS, 1994, 35 (04) : 575 - 578
[2] ASYMMETRIC PAUSON-KHAND CYCLIZATION - A FORMAL TOTAL SYNTHESIS OF NATURAL BREFELDIN-A
BERNARDES, V
KANN, N
RIERA, A
MOYANO, A
PERICAS, MA
GREENE, AE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6670 - 6671
[3] OPTICALLY-ACTIVE TRANSITION-METAL COMPLEXES .95. OPTICALLY PURE 3A,4,5,6,7,7A-HEXAHYDRO-2-PHENYL-4,7-METHANO-1H-INDEN-1-ONE VIA THE ASYMMETRIC KHAND REACTION
BLADON, P
PAUSON, PL
BRUNNER, H
EDER, R
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 355 (1-3) : 449 - 454
[4] OPTICALLY-ACTIVE TRANSITION-METAL COMPLEXES .102. ENANTIOSELECTIVE SYNTHESIS OF 3-OXABICYCLO[3.3.0]OCT-7-EN-7-PHENYL-6-ON VIA KHAND-PAUSON REACTION
BRUNNER, H
NIEDERNHUBER, A
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (10) : 711 - 714
[5] ASYMMETRIC APPROACH TO PAUSON-KHAND BICYCLIZATION - ENANTIOSELECTIVE FORMAL SYNTHESIS OF HIRSUTENE
CASTRO, J
SORENSEN, H
RIERA, A
MORIN, C
MOYANO, A
PERICAS, MA
GREENE, AE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) : 9388 - 9389
[6] ASYMMETRIC-SYNTHESIS OF BICYCLO[4.3.0]NONAN-8-ONES BY INTRAMOLECULAR PAUSON-KHAND REACTION
CASTRO, J
MOYANO, A
PERICAS, MA
RIERA, A
GREENE, AE
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (03) : 307 - 310
[7] Asymmetric approach to (+)-beta-cuparenone by intramolecular Pauson-Khand reaction
Castro, J
Moyano, A
Pericas, MA
Riera, A
Greene, AE
AlvarezLarena, A
Piniella, JF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 9016 - 9020
[8] FONQUEMA S, 1997, IN PRESS J AM CHEM S
[9] CYCLOALKENONE SYNTHESIS VIA LEWIS ACID-CATALYZED RETRO DIELS-ALDER REACTIONS OF NORBORNENE DERIVATIVES - SYNTHESIS OF 12-OXOPHYTODIENOIC ACID
GRIECO, PA
ABOOD, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) : 6008 - 6010
[10] Harrington P. J., 1990, TRANSITION METALS TO, P259

← 1 2 3 →