Platinum(0)-catalyzed carbonylative lactonization of 5-hydroxy-1-pentyne with carbon monoxide in the presence of thiols

被引:38
作者
Ogawa, A [1 ]
Kawabe, K
Kawakami, J
Mihara, M
Hirao, T
Sonoda, N
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Osaka 5650871, Japan
[2] Kansai Univ, Fac Engn, Dept Appl Chem, Osaka 5640073, Japan
关键词
D O I
10.1021/om9801857
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Tetrakis (triphenylphosphine)platinum (O) (Pt(PPh3)(4)) in the presence of aromatic thiols exhibits an excellent catalytic activity toward the carbonylative lactonization, of 5-hydroxy-1-pentyne with carbon, monoxide, which provides alpha-methylene-delta-lactone in good yield.
引用
收藏
页码:3111 / 3114
页数:4
相关论文
共 16 条
[1]  
Colquhoun H. M., 1991, CARBONYLATION DIRECT, P173
[2]   SYNTHESIS OF ALPHA-METHYLENE LACTONES BY REDUCTIVE AMINATION OF ALPHA-FORMYL LACTONES - SCOPE AND LIMITATIONS [J].
HARMON, AD ;
HUTCHINSON, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (24) :3474-3480
[3]  
HARMON AD, 1973, TETRAHEDRON LETT, P1293
[4]   METHOD FOR SYNTHESIS OF UNSATURATED CARBONYL-COMPOUNDS [J].
KSANDER, GM ;
MCMURRY, JE ;
JOHNSON, M .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (07) :1180-1185
[5]   PALLADIUM-CATALYZED CARBONYLATION - A NEW SYNTHESIS OF ALPHA-METHYLENE GAMMA-LACTAMS, ALPHA-METHYLENE DELTA-LACTAMS, AND ALPHA-METHYLENE EPSILON-LACTAMS AND ALPHA-METHYLENE GAMMA-LACTONES, ALPHA-METHYLENE DELTA-LACTONES, AND ALPHA-METHYLENE EPSILON-LACTONES INCLUDING BICYCLIC LACTAMS OF PYRROLIZIDINE AND INDOLIZIDINE SKELETONSAL [J].
MORI, M ;
WASHIOKA, Y ;
URAYAMA, T ;
YOSHIURA, K ;
CHIBA, K ;
BAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4058-4067
[6]  
MURRAY AW, 1984, J CHEM SOC CHEM COMM, P12
[7]   DESIGN AND MECHANISM OF PALLADIUM CATALYSTS FOR SYNTHESIS OF METHYLENE LACTONES BY CYCLOCARBONYLATION OF ACETYLENIC ALCOHOLS [J].
MURRAY, TF ;
NORTON, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (15) :4107-4119
[8]  
MURRAY TF, 1977, J AM CHEM SOC, V99, P8085, DOI 10.1021/ja00466a070
[9]   PALLADIUM-CATALYZED CYCLOCARBONYLATION OF ACETYLENIC ALCOHOLS TO METHYLENE LACTONES - SCOPE AND SYNTHESIS OF APPROPRIATE SUBSTRATES [J].
MURRAY, TF ;
SAMSEL, EG ;
VARMA, V ;
NORTON, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (25) :7520-7528
[10]   CYCLO-CARBONYLATION OF 2-EXO-ETHYNYL-7-SYN-NORBORNANOL TO AN ALPHA-METHYLENE DELTA-LACTONE [J].
MURRAY, TF ;
VARMA, V ;
NORTON, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) :353-355