Tandem cyclopropanation/ring-closing metathesis of dienynes

被引：80

作者：

Peppers, BP ^{[1
]}

Diver, ST ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 31期

关键词：

D O I：

10.1021/ja049079o

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Certain dienynes give cyclorearrangement by tandem cyclopropanation/ring-closing alkene metathesis, triggered by either a ruthenium carbene or noncarbene ruthenium(II) precatalyst. The process represents a variation of enyne metathesis where presumed cyclopropyl carbene intermediates undergo a consecutive ring-closing metathesis. A mechanistic proposal is offered, and sequential use of catalysts provided a tandem ring-closing enyne/alkene metathesis product. Copyright © 2004 American Chemical Society.

引用

页码：9524 / 9525

页数：2

共 16 条

[1] The behavior of 1,n-enynes in the presence of transition metals
Aubert, C
Buisine, O
Malacria, M
[J]. CHEMICAL REVIEWS, 2002, 102 (03) : 813 - 834
[2] Skeletal reorganization of enynes to 1-vinylcycloalkenes catalyzed by GaCl3
Chatani, N
Inoue, H
Kotsuma, T
Murai, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) : 10294 - 10295
[3] Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization of ene-ene-ynes. Interception of a carbenoid intermediate in skeletal reorganization of enynes
Chatani, N
Kataoka, K
Murai, S
Furukawa, N
Seki, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) : 9104 - 9105
[4] Enyne metathesis (enyne bond reorganization)
Diver, ST
Giessert, AJ
[J]. CHEMICAL REVIEWS, 2004, 104 (03) : 1317 - 1382
[5] Novel rearrangements of enynes catalyzed by PtCl2
Fürstner, A
Szillat, H
Stelzer, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) : 6785 - 6786
[6] Platinum- and acid-catalyzed enyne metathesis reactions:: Mechanistic studies and applications to the syntheses of streptorubin B and metacycloprodigiosin
Fürstner, A
Szillat, H
Gabor, B
Mynott, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) : 8305 - 8314
[7] KINOSHITA A, 1994, SYNLETT, P1020
[8] Unexpected results of enyne metathesis using a ruthenium complex containing an N-heterocyclic carbene ligand
Kitamura, T
Sato, Y
Mori, M
[J]. CHEMICAL COMMUNICATIONS, 2001, (14) : 1258 - 1259
[9] Addition of diazoalkanes to enynes promoted by a ruthenium catalyst:: Simple synthesis of alkenyl bicyclo[3.1.0]hexane derivatives
Monnier, F
Castillo, D
Dérien, S
Toupet, L
Dixneuf, PH
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) : 5474 - 5477
[10] NEW CHIRAL RUTHENIUM BIS(OXAZOLINYL)PYRIDINE CATALYST - EFFICIENT ASYMMETRIC CYCLOPROPANATION OF OLEFINS WITH DIAZOACETATES
NISHIYAMA, H
ITOH, Y
MATSUMOTO, H
PARK, SB
ITOH, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) : 2223 - 2224

← 1 2 →