STEREOSELECTIVE SYNTHESIS OF BETA-LACTONES CONTAINING ALPHA-Z-ALKOXYCARBONYLMETHYLENE CHAINS BY PALLADIUM-CATALYZED OXIDATIVE CARBONYLATION OF TERTIARY ALPHA-HYDROXYALKYNES

被引：33

作者：

GABRIELE, B ^{[1
]}

COSTA, M ^{[1
]}

SALERNO, G ^{[1
]}

CHIUSOLI, GP ^{[1
]}

机构：

[1] UNIV PARMA,DIPARTIMENTO CHIM ORGAN & IND,I-43100 PARMA,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 12期

关键词：

D O I：

10.1039/c39940001429

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tertiary alpha-hydroxyalkynes undergo oxidative carbonylation in alcohols in the presence of catalytic amounts of Pdl(2)-Kl to give beta-lactones derived from alkoxycarbonylation at the terminal carbon of the alkyne and cis-carbonylation at the internal carbon, followed by carbonyl trapping by the tertiary hydroxy group.

引用

页码：1429 / 1430

页数：2

共 7 条

[1] BRANDSMA I, 1971, PREPARATIVE ACETYLEN, P65
[2] AN EFFICIENT AND SELECTIVE PALLADIUM-CATALYZED OXIDATIVE DICARBONYLATION OF ALKYNES TO ALKYL-MALEIC OR ARYL-MALEIC ESTERS
GABRIELE, B
COSTA, M
SALERNO, G
CHIUSOLI, GP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (01): : 83 - 87
[3] INGOLD CK, 1921, J CHEM SOC, P119
[4] INGOLD CK, 1921, J CHEM SOC, P951
[5] MATSUDA I, 1990, J AM CHEM SOC, V112, P6121
[6] POMMIER A, 1993, SYNTHESIS-STUTTGART, P441
[7] TSUJI J, 1969, TETRAHEDRON, V25, P4099

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