Recent advances in the chemistry of 2-(2-oxoalkylidene)tetrahydrofurans

被引：34

作者：

Bellur, Esen ^{[1
]}

Feist, Holger ^{[1
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany

来源：

TETRAHEDRON | 2007年 / 63卷 / 45期

关键词：

cyclizations; dianions; tetrahydrofurans; beta-ketoesters; O-heterocycles; silyl enol ethers;

D O I：

10.1016/j.tet.2007.08.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization of 1,3-dicarbonyl dianions ('free dianions') and 1,3-bis-silyl enol ethers ('masked dianions') with various 1,2-dielectrophiles provides an efficient strategy for the synthesis of 2-alkylidenetetrahydrofurans, which represent useful synthetic building blocks. 2-Alkylidenetetrahydrofurans can be functionalized by lithiation and subsequent alkylation, NBS-mediated bromination and subsequent palladium-catalyzed cross-coupling, BBr3-mediated ring cleavage, elimination, dehydrogenation, palladium-catalyzed rearrangement, hydrogenation, Claisen rearrangements, and enzymatic kinetic resolution. © 2007 Elsevier Ltd. All rights reserved.

引用

页码：10865 / 10888

页数：24

共 266 条

[1] The synthesis of pyrimidin-4-yl substituted α-amino acids.: A versatile approach from alkynyl ketones
Adlington, RM
Baldwin, JE
Catterick, D
Pritchard, GJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08): : 855 - 866
[2] STEREOCONTROL USING SILICON - A SYNTHESIS OF METHYL (+)-NONACTATE
AHMAR, M
DUYCK, C
FLEMING, I
[J]. PURE AND APPLIED CHEMISTRY, 1994, 66 (10-11) : 2049 - 2052
[3] Predisposition in synthesis:: efficient routes to (±)-untenone A and (±)-manzamenones A, C and F
Al-Busafi, S
Whitehead, RC
[J]. TETRAHEDRON LETTERS, 2000, 41 (18) : 3467 - 3470
[4] UPSILON-TRIAZOLINES .19. THIOCINO[4,5-D]-1,2,3-TRIAZOLE AND THIOCINO[4,5-D]ISOXAZOLE DERIVATIVES
ALMIRANTE, N
FORTI, L
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) : 1121 - 1123
[5] ALTEL TH, 1995, LIEBIGS ANN, P689
[6] EFFICIENT ACCESS TO POLYFUNCTIONALIZED AND POLYCYCLIC FURANOIDS - CONTROL OF THE OFF-TEMPLATE CENTER VIA ACID CATALYSIS
ALTEL, TH
VOELTER, W
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) : 239 - 240
[7] One biocatalyst - Many applications: The use of Candida antarctica B-lipase in organic synthesis
Anderson, EM
Karin, M
Kirk, O
[J]. BIOCATALYSIS AND BIOTRANSFORMATION, 1998, 16 (03) : 181 - 204
[8] ARAI K, 1989, CHEM PHARM BULL, V37, P3229
[9] FURANNULATION STRATEGY FOR SYNTHESIS OF THE NATURALLY-OCCURRING FUSED 3-METHYLFURANS - EFFICIENT SYNTHESIS OF EVODONE AND MENTHOFURAN AND REGIOSELECTIVE SYNTHESIS OF MATURONE VIA A LEWIS-ACID CATALYZED DIELS-ALDER REACTION - SOME COMMENTS FOR ITS MECHANISTIC ASPECTS
ASO, M
OJIDA, A
YANG, G
CHA, OJ
OSAWA, E
KANEMATSU, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) : 3960 - 3968
[10] A novel catalytic and highly enantioselective approach for the synthesis of optically active carbohydrate derivatives
Audrain, H
Thorhauge, J
Hazell, RG
Jorgensen, KA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) : 4487 - 4497

← 1 2 3 4 5 6 7 8 9 10 →