Silver-catalyzed cyclization of acetylenic alcohols and acids: a remarkable accelerating effect of a propargylic C-O bond

被引：65

作者：

Dalla, V

Pale, P

机构：

[1] Univ Reims, Chim Phys Organ Lab, CNRS, UMR 6519, F-51100 Reims, France

[2] Univ Strasbourg 1, Inst Le Bel, CNRS, Lab React & Synth Organ,UMR 7509, F-67000 Strasbourg, France

来源：

NEW JOURNAL OF CHEMISTRY | 1999年 / 23卷 / 08期

关键词：

D O I：

10.1039/a903587g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The heteroannulation catalyzed by silver salts of alkynols 1, 2 or alkynoic acids 3 is considerably enhanced by the presence of a propargylic C-O bond, This method allows for a rapid access to highly functionalized heterocycles, such as alpha-methylene oxolanes 4 or oxanes 5 and as gamma-methylene pentanolactones 6.

引用

页码：803 / 805

页数：3

共 12 条

[1] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS
BOIVIN, TLB
[J]. TETRAHEDRON, 1987, 43 (15) : 3309 - 3362
[2] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES
CARDILLO, G
ORENA, M
[J]. TETRAHEDRON, 1990, 46 (10) : 3321 - 3408
[3] SILVER-CATALYZED HETEROCYCLIZATION - FIRST TOTAL SYNTHESIS OF THE NATURALLY-OCCURRING CIS 2-HEXADECYL-3-HYDROXY-4-METHYLENE BUTYROLACTONE
DALLA, V
PALE, P
[J]. TETRAHEDRON LETTERS, 1994, 35 (21) : 3525 - 3528
[4] Chemistry of 3,4-epoxy-2-methylene oxolanes: A new synthesis of furanes and dihydrofuranes
Dalla, V
Pale, P
[J]. TETRAHEDRON LETTERS, 1996, 37 (16) : 2781 - 2784
[5] DIASTEREOSELECTIVE SYNTHESIS OF SPIROKETALS VIA RADICAL CYCLIZATION
DALLA, V
PALE, P
[J]. TETRAHEDRON LETTERS, 1992, 33 (51) : 7857 - 7860
[6] Chemistry of 3,4-epoxy-2-methylene oxolanes: Highly diastereoselective electrophilic additions.
Dalla, V
Pale, P
[J]. TETRAHEDRON LETTERS, 1996, 37 (16) : 2777 - 2780
[7] FUKUDA Y, 1987, HETEROCYCLES, V25, P297
[8] STEREOSELECTIVE SYNTHESIS OF OLIGO-TETRAHYDROFURANS
KOERT, U
[J]. SYNTHESIS-STUTTGART, 1995, (02): : 115 - 132
[9] SILVER ASSISTED HETEROCYCLIZATION OF ACETYLENIC-COMPOUNDS
PALE, P
CHUCHE, J
[J]. TETRAHEDRON LETTERS, 1987, 28 (51) : 6447 - 6448
[10] PI-FACIAL DIASTEREOSELECTION IN [4+2]-CYCLOADDITIONS OF 3,4-EPOXY-2-METHYLENEOXOLANES WITH OXADIENES - A SHORT SYNTHESIS OF SPIROKETALS
PALE, P
BOUQUANT, J
CHUCHE, J
CARRUPT, PA
VOGEL, P
[J]. TETRAHEDRON, 1994, 50 (27) : 8035 - 8052

← 1 2 →