ALKYNYLATIONS OF OXIRANES WITH LITHIUM ACETYLIDES BY THE CATALYSIS OF TRIMETHYLGALLIUM

被引：14

作者：

FUKUDA, Y ^{[1
]}

MATSUBARA, S ^{[1
]}

LAMBERT, C ^{[1
]}

SHIRAGAMI, H ^{[1
]}

NANKO, T ^{[1
]}

UTIMOTO, K ^{[1
]}

NOZAKI, H ^{[1
]}

机构：

[1] KYOTO UNIV, FAC ENGN, DEPT, KYOTO 606, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1991年 / 64卷 / 06期

关键词：

D O I：

10.1246/bcsj.64.1810

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of 1-lithio-1-alkynes with oxiranes under the catalytic action of trimethylgallium afforded the corresponding beta-hydroxy acetylenic compounds in good yields with excellent regioselectivities. No isomerization of oxiranes was observed during the reactions because of low Lewis acidity of trimethylgallium. The mechanism including activation of an oxirane by the coordination to trimethylgallium was proposed.

引用

页码：1810 / 1813

页数：4

共 16 条

[1] FUNCTIONALIZED ALANES FOR CONVERSION OF EPOXIDES TO TRANS-FUSED GAMMA-LACTONES
DANISHEFSKY, S
KITAHARA, T
TSAI, M
DYNAK, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (09) : 1669 - 1671
[2] MECHANISM AND SYNTHETIC UTILITY OF BORON-TRIFLUORIDE ETHERATE PROMOTED ORGANO-LITHIUM ADDITIONS
EIS, MJ
WROBEL, JE
GANEM, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) : 3693 - 3694
[3] FAUCOUNAU L, 1934, CR HEBD ACAD SCI, V199, P605
[4] FRIED J, 1969, TETRAHEDRON LETT, P1379
[5] HANACK M, 1978, SYNTHESIS-STUTTGART, P26
[6] REACTION OF CYANOTRIMETHYLSILANE WITH OXIRANES - EFFECTS OF CATALYSTS OR MEDIATORS ON REGIOSELECTIVITY AND AMBIDENT CHARACTER
IMI, K
YANAGIHARA, N
UTIMOTO, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) : 1013 - 1016
[7] A NEW STEREOSPECIFIC ROUTE TO ALPHA-ALKYLIDENE GAMMA-LACTONES
JACKSON, WR
PERLMUTTER, P
SMALLRIDGE, AJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (21) : 1509 - 1510
[8] JAGER V, 1977, METHODEN ORG CHEM, V5
[9] NORMANT H, 1957, B SOC CHIM FR, P1447
[10] STRUCTURE ACTIVITY RELATIONSHIPS AMONG AROMATIC ANALOGS OF TRAIL-FOLLOWING PHEROMONE OF SUBTERRANEAN TERMITES
PRESTWICH, GD
ENG, WS
DEATON, E
WICHERN, D
[J]. JOURNAL OF CHEMICAL ECOLOGY, 1984, 10 (08) : 1201 - 1217

← 1 2 →