Silylcarbocyclizations of 1,6-diynes

被引：69

作者：

Ojima, I ^{[1
]}

Zhu, JW ^{[1
]}

Vidal, ES ^{[1
]}

Kass, DF ^{[1
]}

机构：

[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 27期

关键词：

D O I：

10.1021/ja980907l

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two types of silylcarbocyclization reactions (SiCaCs) of 1,6-diynes are discussed: (i) silylcarbocyclization-hydrosilylation (SiCaC-HS) reactions giving 3-(silylmethylene)-4-(silylmethyl)pyrrolidine, 3-(silylmethylene)-4-(silylmethyl)tetrahydrofuran, 3,4-bis(silylmethyl)-3-pyrroline, and 1,2-bis(silylmethyl)-4,4-dicarbethoxycyclopentene; and (ii) silylcarbobicyclization (SiCaB) reactions yielding a variety of carbocyclic and heterocyclic bicyclo[3.3.0] systems. Mechanisms for these SiCaC-HS and SiCaB processes are proposed.

引用

页码：6690 / 6697

页数：8

共 52 条

[1] DIASTEREOSELECTIVE ZIRCONOCENE-PROMOTED BICYCLIZATION-CARBONYLATION OF ALLYLICALLY METHYL-SUBSTITUTED ENYNES - SYNTHESIS OF (+)-IRIDOMYRMECIN
AGNEL, G
OWCZARCZYK, Z
NEGISHI, E
[J]. TETRAHEDRON LETTERS, 1992, 33 (12) : 1543 - 1546
[2] TITANOCENE-CATALYZED CONVERSION OF ENYNES TO BICYCLIC CYCLOPENTENONES
BERK, SC
GROSSMAN, RB
BUCHWALD, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) : 4912 - 4913
[3] Chatani N, 1996, SYNLETT, P414
[4] HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE SILYLFORMYLATION OF ALKYNES UNDER MILD CONDITIONS PROMOTED BY DIRHODIUM(II) PERFLUOROBUTYRATE
DOYLE, MP
SHANKLIN, MS
[J]. ORGANOMETALLICS, 1994, 13 (04) : 1081 - 1088
[5] HIGHLY EFFICIENT REGIOSELECTIVE SILYLCARBONYLATION OF ALKYNES CATALYZED BY DIRHODIUM(II) PERFLUOROBUTYRATE
DOYLE, MP
SHANKLIN, MS
[J]. ORGANOMETALLICS, 1993, 12 (01) : 11 - 12
[6] MACROCYCLIC ACETYLENIC COMPOUNDS .1. CYCLOTETRADECA-1,3-DIYNE AND RELATED COMPOUNDS
EGLINTON, G
GALBRAITH, AR
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1959, (MAR): : 889 - 896
[7] SYNTHESIS OF PYRROLIZIDINE ALKALOIDS VIA RHODIUM-CATALYZED SILYLFORMYLATION AND AMIDOCARBONYLATION
EGUCHI, M
ZENG, QP
KORDA, A
OJIMA, I
[J]. TETRAHEDRON LETTERS, 1993, 34 (06) : 915 - 918
[8] ENEFFRAIM DA, 1973, TETRAHEDRON, V25, P4041
[9] EPSZTEIN R, 1956, B SOC CHIM FR, P158
[10] REDUCTIVE CYCLIZATION OF ESTER-CONTAINING ENYNES WITH A PRACTICAL TITANOCENE REAGENT - SYNTHESIS OF BICYCLIC CYCLOPENTENONES AND IMINOCYCLOPENTENES
GROSSMAN, RB
BUCHWALD, SL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5803 - 5805

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