Synthesis of spirosystems by rhodium(II)-carbenoid C-H insertion reactions.

被引：14

作者：

Aburel, PS ^{[1
]}

Undheim, K ^{[1
]}

机构：

[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 22期

关键词：

D O I：

10.1016/S0040-4039(98)00591-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple one-pot procedure is described for the preparation of spiro[4,4]nonane-2,7-dione derivatives from open chain bis(alpha-diazoketones). The reactions proceed by an intramolecular Rh(II)-carbenoid insertion into a methylene C-H bond yielding a cyclopentane which subsequently undergoes C-H methine insertion and cyclopentyl spiroannulation. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3813 / 3814

页数：2

共 12 条

[1] RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS
ADAMS, J
SPERO, DM
[J]. TETRAHEDRON, 1991, 47 (10-11) : 1765 - 1808
[2] REDUCTIVE CYCLIZATION OF MERCURIAL ENONES
DANISHEFSKY, S
CHACKALAMANNIL, S
UANG, BJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) : 2231 - 2232
[3] FAHR E, 1960, LIEBIGS ANN CHEM, V638, P1
[4] Ruthenium-catalyzed enyne metathesis in stereoselective preparation of cyclic 1-amino-1-carboxylic acids.
Hammer, K
Undheim, K
[J]. TETRAHEDRON, 1997, 53 (30) : 10603 - 10614
[5] Ruthenium(II) in ring closing metathesis for the stereoselective preparation of cyclic 1-amino-1-carboxylic acids.
Hammer, K
Undheim, K
[J]. TETRAHEDRON, 1997, 53 (06) : 2309 - 2322
[6] DIRHODIUM(II) TETRA(TRIPHENYLACETATE) - A HIGHLY EFFICIENT CATALYST FOR THE SITE-SELECTIVE INTRAMOLECULAR C-H INSERTION REACTIONS OF ALPHA-DIAZO BETA-KETO-ESTERS
HASHIMOTO, S
WATANABE, N
IKEGAMI, S
[J]. TETRAHEDRON LETTERS, 1992, 33 (19) : 2709 - 2712
[7] Coloured compounds from plants XLVI. Constitution of crocetins and bixins. Synthesis of perhydro-norbixins
Karrer, P
Benz, F
Morf, R
Raudnitz, H
Stoll, M
Takahashi, T
[J]. HELVETICA CHIMICA ACTA, 1932, 15 : 1399 - 1419
[8] AN IMPROVED SYNTHESIS AND RESOLUTION OF (+/-)-CIS,CIS-SPIRO[4.4]NONANE-1,6-DIOL
NIEMAN, JA
PARVEZ, M
KEAY, BA
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (09) : 1973 - 1976
[9] PADWA A, 1992, TETRAHEDRON, V48, P5383
[10] SPIRO[4.4]NONATETRAENE AND SPIRO[4.4]NONA-1,3,7-TRIENE - SYNTHESIS AND PROPERTIES - EFFECTS OF SPIROCONJUGATION
SEMMELHACK, MF
FOOS, JS
KATZ, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) : 7325 - 7336

← 1 2 →