Three-carbon ring-enlargement of ethereal oxonium ylides - A viable synthesis of medium-sized cyclic ketoethers

被引：15

作者：

Oku, A

Ohki, S

Yoshida, T

Kimura, K

机构：

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 09期

关键词：

D O I：

10.1039/cc9960001077

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Eight- to eleven-membered cyclic ketoethers are synthesized in a single-step by rhodium(II)-catalysed three-carbon ring-enlargement of diazoacetonyl-substituted cyclic ethers via bicyclic ethereal oxonium ylide intermediates.

引用

页码：1077 / 1078

页数：2

共 12 条

[1] A STRATEGY FOR THE ASYMMETRIC-SYNTHESIS OF MEDIUM RING OXYGEN HETEROCYCLES - ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-OCTAHYDRODEACETYLDEBROMOLAURENCIN
CLARK, JS
HOLMES, AB
[J]. TETRAHEDRON LETTERS, 1988, 29 (34) : 4333 - 4336
[2] SYNTHESIS OF CYCLIC ETHERS FROM COPPER CARBENOIDS BY FORMATION AND REARRANGEMENT OF OXONIUM YLIDES
CLARK, JS
KROWIAK, SA
STREET, LJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (27) : 4385 - 4388
[3] DAVIES MJ, 1990, SYNLETT, P93
[4] OXYGEN YLIDES .1. REACTIONS OF CARBENES WITH OXETANE
FRIEDRICH, K
JANSEN, U
KIRMSE, W
[J]. TETRAHEDRON LETTERS, 1985, 26 (02) : 193 - 196
[5] Selectivity in the ring-expansion and ring-switching reactions of bicyclooxonium ions
Kamada, T
GeQing
Abe, M
Oku, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (05): : 413 - 416
[6] ONE-POT SYNTHESIS OF ALPHA-MONO-SUBSTITUTED AND ALPHA,ALPHA-DISUBSTITUTED CYCLIC ETHERS FROM LACTONES
MUKAIYAMA, T
HOMMA, K
TAKENOSHITA, H
[J]. CHEMISTRY LETTERS, 1988, (10) : 1725 - 1728
[7] Formation of oxonium ylide evidenced by the laser flash photolysis of (biphenyl-4-yl)chlorodiazirine in ethers
Naito, I
Oku, A
Otani, N
Fujiwara, Y
Tanimoto, Y
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (04): : 725 - 729
[8] REACTION OF CARBENES WITH CYCLIC ETHERS IN THE PRESENCE OF NUCLEOPHILES - A 3-COMPONENT COUPLING REACTION
OKU, A
KIMURA, K
OHWAKI, S
[J]. ACTA CHEMICA SCANDINAVICA, 1993, 47 (04): : 391 - 397
[9] GENERATION AND UTILIZATION OF CARBONYL YLIDES VIA THE TANDEM CYCLIZATION CYCLOADDITION METHOD
PADWA, A
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (01) : 22 - 28
[10] PADWA A, 1991, CHEM REV, V91, P281

← 1 2 →