Mild and efficient palladium(II)-catalyzed racemization of allenes

被引:42
作者
Horváth, A [1 ]
Bäckvall, JE [1 ]
机构
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
关键词
D O I
10.1039/b316482a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Allenes undergo racemization in the presence of catalytic amounts of Pd(OAC)(2)/LiBr under mild conditions; the reaction proceeds via a bromopalladation-debromopalladation sequence and tolerates various functional groups.
引用
收藏
页码:964 / 965
页数:2
相关论文
共 25 条
[1]   Dynamic kinetic resolution with enzyme and palladium combinations [J].
Allen, JV ;
Williams, JMJ .
TETRAHEDRON LETTERS, 1996, 37 (11) :1859-1862
[2]   Dynamic kinetic resolution of acyclic allylic acetates using lipase and palladium [J].
Choi, YK ;
Suh, JH ;
Lee, D ;
Lim, IT ;
Jung, JY ;
Kim, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8423-8424
[3]   Primary allenic alcohols of high optical purity via lipase catalyzed resolution [J].
Cipiciani, A ;
Bellezza, F .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2002, 17 (06) :261-266
[4]   ALLENES AND ACETYLENES .23. SYNTHESIS OF ALPHA-ALLENIC AMINES VIA ALLENIC IMINES OBTAINED FROM ORGANOCOPPER REACTIONS [J].
CLAESSON, A ;
SAHLBERG, C .
TETRAHEDRON, 1982, 38 (03) :363-368
[5]   CHIRAL ALLENES ARE RACEMIZED BY ORGANOCUPRATES [J].
CLAESSON, A ;
OLSSON, LI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (12) :524-525
[6]  
COWIE JS, 1973, J CHEM SOC PERK T, V7, P720
[7]   STEREOSPECIFIC TOTAL SYNTHESIS OF THE CYCLOHEXENE OXIDE ANTIBIOTIC EUPENOXIDE [J].
DUKE, RK ;
RICKARDS, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (11) :1898-1904
[8]   Controlled racemization of optically active organic compounds: Prospects for asymmetric transformation [J].
Ebbers, EJ ;
Ariaans, GJA ;
Houbiers, JPM ;
Bruggink, A ;
Zwanenburg, B .
TETRAHEDRON, 1997, 53 (28) :9417-9476
[9]   SYNTHESIS AND STEREOCHEMISTRY OF ALLENES .3. HIGHLY STEREOSELECTIVE SYNTHESIS OF CHIRAL ALKYLALLENES BY ORGANOCOPPER(I)-INDUCED ANTI 1,3-SUBSTITUTION OF CHIRAL PROPYNYL ESTERS [J].
ELSEVIER, CJ ;
VERMEER, P .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3726-3730
[10]   LIPASE-CATALYZED ESTER FORMATION IN ORGANIC-SOLVENTS - PARTIAL RESOLUTION OF PRIMARY ALLENIC ALCOHOLS [J].
GIL, G ;
FERRE, E ;
MEOU, A ;
LEPETIT, J ;
TRIANTAPHYLIDES, C .
TETRAHEDRON LETTERS, 1987, 28 (15) :1647-1648