Enantioselective isomerization of allylamine to enamine: practical asymmetric synthesis of (-)-menthol by Rh-BINAP catalysts

被引:46
作者
Akutagawa, S [1 ]
机构
[1] Takasago Int Corp, Minato Ku, Tokyo 108, Japan
关键词
allylamine; asymmetric synthesis; BINAP; chiral ligand; homogeneous catalysis; isomerization; isoprenoid amine; (-)-menthol; rhodium;
D O I
10.1023/A:1019112911246
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Enantioselective isomerizations of allylamines to enamines are summarized from idea to industry. The Rh-BINAP catalyst reveals high selectivities, 99% yield and 98% enantiomer excess and high activity, TON > 400,000. Its industrial use for the production of a 1,500 t/y scale of (-)-menthol is introduced emphasizing technical development.
引用
收藏
页码:271 / 274
页数:4
相关论文
共 9 条
[1]   ASYMMETRIC-SYNTHESIS BY METAL BINAP CATALYSTS [J].
AKUTAGAWA, S .
APPLIED CATALYSIS A-GENERAL, 1995, 128 (02) :171-207
[2]  
AKUTAGAWA S, 1993, CATALYTIC ASYMMETRIC, pCH4
[3]  
AKUTAGAWA S, 1992, CHIRALITY IND COMMER, pCH16
[4]   METAL-ASSISTED TERPENOID SYNTHESES .6. ENANTIOSELECTIVE HYDROGEN MIGRATION IN PROCHIRAL ALLYLAMINE SYSTEMS BY CHIRAL COBALT CATALYSTS [J].
KUMOBAYASHI, H ;
AKUTAGAWA, S ;
OTSUKA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (12) :3949-3950
[5]  
TAKABE K, 1972, TETRAHEDRON LETT, P4009
[6]   PRACTICAL SYNTHESIS OF (R)-2,2' OR (S)-2,2'-BIS(DIARYLPHOSPHINO)-1,1'-BINAPHTHYLS (BINAPS) [J].
TAKAYA, H ;
MASHIMA, K ;
KOYANO, K ;
YAGI, M ;
KUMOBAYASHI, H ;
TAKETOMI, T ;
AKUTAGAWA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :629-635
[7]   BIS[(R)-(+)-BINAP]RHODIUM(I) PERCHLORATE, A HIGHLY EFFICIENT CATALYST FOR THE ASYMMETRIC ISOMERIZATION OF ALLYLAMINES [J].
TANI, K ;
YAMAGATA, T ;
TATSUNO, Y ;
YAMAGATA, Y ;
TOMITA, K ;
AKUTAGAWA, S ;
KUMOBAYASHI, H ;
OTSUKA, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (03) :217-219
[8]   METAL-ASSISTED TERPENOID SYNTHESIS .7. HIGHLY ENANTIOSELECTIVE ISOMERIZATION OF PROCHIRAL ALLYLAMINES CATALYZED BY CHIRAL DIPHOSPHINE RHODIUM(I) COMPLEXES - PREPARATION OF OPTICALLY-ACTIVE ENAMINES [J].
TANI, K ;
YAMAGATA, T ;
AKUTAGAWA, S ;
KUMOBAYASHI, H ;
TAKETOMI, T ;
TAKAYA, H ;
MIYASHITA, A ;
NOYORI, R ;
OTSUKA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (18) :5208-5217
[9]  
YAMAKAWA M, 1992, ORGANOMETALLICS, V11, P3167