NEW ACCESS TO DI-EXO-METHYLENECYCLOBUTANES VIA [2+2] CYCLOADDITION OF 3-METHYLTHIO-4-TRIMETHYLSILYL-1,2-BUTADIENE WITH ALKENES MEDIATED BY A LEWIS-ACID

被引：36

作者：

HOJO, M ^{[1
]}

TOMITA, K ^{[1
]}

HIROHARA, Y ^{[1
]}

HOSOMI, A ^{[1
]}

机构：

[1] UNIV TSUKUBA,DEPT CHEM,TSUKUBA,IBARAKI 305,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 50期

关键词：

2 + 2] CYCLOADDITION; ALLENYLMETHYLSILANE; 1,2,3-BUTATRIENE; DI-EXO-METHYLENECYCLOBUTANE; ALLENYL SULFIDE; 4+3] CYLOADDITION;

D O I：

10.1016/S0040-4039(00)61469-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methylthio-substituted allenylmethylsilane, a kind of allylsilane, undergoes only [2 + 2] cycloaddition reaction with alkenes mediated by a Lewis acid to afford the corresponding methylenecyclobutanes which are readily converted to di-exo-methylenecyclobutanes by rite sequential oxidation-1,2-elimination in good yield. Di-exo-methylenecyclobutane is also successfully applied to construct a bicyclo[5.2.0]nonenone skeleton by the reaction with 2-oxyallyl cation.

引用

页码：8123 / 8126

页数：4

共 16 条

[11] ORGANIC-SYNTHESIS UTILIZING CHARACTERISTICS OF ORGANOSILICON COMPOUNDS
HOSOMI, A
HOJO, M
[J]. YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1992, 112 (03): : 147 - 160
[12] HOSOMI A, 1989, ADV PHARM SCI, V5, P80
[13] HOSOMI A, 1992, REV HETEROATOM CHEM, V7, P214
[14] ASYMMETRIC [2 + 2] CYCLOADDITION REACTION CATALYZED BY A CHIRAL TITANIUM REAGENT
NARASAKA, K
HAYASHI, Y
SHIMADZU, H
NIIHATA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) : 8869 - 8885
[15] NOYORI R, 1971, J AM CHEM SOC, V93, P1213
[16] NOYORI R, ORGANIC SYNTH COLL, V6, P520

← 1 2 →