Synthesis of oxygenated heterocycles from cyclic allylsiloxanes using ring-closing olefin metathesis

被引：74

作者：

Meyer, C

Cossy, J

机构：

[1] Laboratoire de Chimie Organique, Associé Au CNRS, ESPCI, 10 rue Vauquelin

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(97)10147-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic allylsiloxanes were prepared from allyldimethylsilyl ethers of various alkenols by using a catalytic ring-closing metathesis (RCM) reaction. The transformation of these cyclic allylsiloxanes into stereoselectively substituted tetrahydrofurans and tetrahydropyrans was achieved by using a silyl modified Sakurai reaction. (C) 1997 Elsevier Science Ltd.

引用

页码：7861 / 7864

页数：4

共 17 条

[1] Highly functionalised monocyclic and bicyclic beta-lactams via alkene metathesis
Barrett, AGM
Baugh, SPD
Gibson, VC
Giles, MR
Marshall, EL
Procopiou, PA
[J]. CHEMICAL COMMUNICATIONS, 1997, (02) : 155 - 156
[2] THE FIRST SYNTHESIS OF THE ABCD RING-SYSTEM OF MANZAMINE-A - CONSTRUCTION OF THE MACROCYCLIC RING-D
BORER, BC
DEERENBERG, S
BIERAUGEL, H
PANDIT, UK
[J]. TETRAHEDRON LETTERS, 1994, 35 (19) : 3191 - 3194
[3] A simple method to polyhydroxylated olefinic molecules using ring-closing olefin metathesis
Chang, SB
Grubbs, RH
[J]. TETRAHEDRON LETTERS, 1997, 38 (27) : 4757 - 4760
[4] SYNTHESIS OF NITROGEN-HETEROCYCLES VIA CATALYTIC RING-CLOSING METATHESIS OF DIENES
FU, GC
GRUBBS, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) : 7324 - 7325
[5] THE APPLICATION OF CATALYTIC RING-CLOSING OLEFIN METATHESIS TO THE SYNTHESIS OF UNSATURATED OXYGEN HETEROCYCLES
FU, GC
GRUBBS, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) : 5426 - 5427
[6] CATALYTIC RING CLOSING METATHESIS OF DIENYNES - CONSTRUCTION OF FUSED BICYCLIC RINGS
KIM, SH
BOWDEN, N
GRUBBS, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) : 10801 - 10802
[7] THE INTRAMOLECULAR SILYL-MODIFIED SAKURAI (ISMS) REACTION - STEREOSELECTIVE PREPARATION OF TRI-SUBSTITUTED AND TETRA-SUBSTITUTED TETRAHYDROPYRANS
MARKO, IE
BAYSTON, DJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (41) : 6595 - 6598
[8] THE SILYL MODIFIED SAKURAI (SMS) REACTION - AN EFFICIENT AND VERSATILE ONE-POT SYNTHESIS OF HOMOALLYLIC ETHERS
MEKHALFIA, A
MARKO, IE
[J]. TETRAHEDRON LETTERS, 1991, 32 (36) : 4779 - 4782
[9] THE INTRAMOLECULAR SILYL MODIFIED SAKURAI (ISMS) REACTION - A NOVEL AND HIGHLY CONVERGENT SYNTHESIS OF OXOCENES
MEKHALFIA, A
MARKO, IE
ADAMS, H
[J]. TETRAHEDRON LETTERS, 1991, 32 (36) : 4783 - 4786
[10] GRIGNARD-TYPE CARBONYL ADDITION OF ALLYL HALIDES BY MEANS OF CHROMOUS SALT - CHEMOSPECIFIC SYNTHESIS OF HOMOALLYL ALCOHOLS
OKUDE, Y
HIRANO, S
HIYAMA, T
NOZAKI, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (09) : 3179 - 3181

← 1 2 →