A NOVEL TI(0) INDUCED ALLYLATION OF IMINES IN A TICL4 (CAT) AL BIMETAL SYSTEM - CHIRALITY TRANSFER OF L-VALINE TO HOMOALLYLAMINE

被引:67
作者
TANAKA, H [1 ]
INOUE, K [1 ]
POKORSKI, U [1 ]
TANIGUCHI, M [1 ]
TORII, S [1 ]
机构
[1] OKAYAMA UNIV,FAC ENGN,DEPT APPL CHEM,OKAYAMA 700,JAPAN
关键词
D O I
10.1016/S0040-4039(00)89015-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
"Barbier Type" allylation of imines with allyl bromide has been performed successfully by the action of aluminum (1 equiv.) and titanium(IV)chloride (0.05 equiv.) in THF. The chirality transfer of α-amino acid esters to homoallyl amines is demonstrated by allylation of N-benzalvaline methyl ester followed by alkaline hydrolysis and electrolytic decarboxylation. © 1990.
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页码:3023 / 3026
页数:4
相关论文
共 8 条
[1]   PREPARATION OF 1,2-DIARYLETHYLENEDIAMINES BY AMINATIVE REDUCTIVE COUPLING OF AROMATIC-ALDEHYDES WITH LOW-VALENT TITANIUM REAGENTS [J].
BETSCHART, C ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1987, 70 (08) :2215-2231
[2]   APPLICATION OF ELECTROCHEMICAL RECYCLE OF TI4+-TI3+ TO ADDITIVE DIMERIZATION OF BUTADIENE WITH HYDROXYLAMINE [J].
CHIBA, T ;
TAKATA, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (05) :1418-1421
[3]   NEW REAGENTS FOR INTERMOLECULAR AND INTRAMOLECULAR PINACOLIC COUPLING OF KETONES AND ALDEHYDES [J].
COREY, EJ ;
DANHEISER, RL ;
CHANDRASEKARAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :260-265
[4]   NEW METHOD FOR REDUCTIVE COUPLING OF CARBONYLS TO OLEFINS - SYNTHESIS OF BETA-CAROTENE [J].
MCMURRY, JE ;
FLEMING, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (14) :4708-4709
[5]   TITANIUM-INDUCED DICARBONYL-COUPLING REACTIONS [J].
MCMURRY, JE .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (11) :405-411
[6]   REDUCTIVE COUPLING OF CARBONYL-COMPOUNDS TO PINACOLS AND OLEFINS BY USING TICL4 AND ZN [J].
MUKAIYAMA, T ;
SATO, T ;
HANNA, J .
CHEMISTRY LETTERS, 1973, (10) :1041-1044
[7]  
TYRLIK S, 1973, B SOC CHIM FR II-CH, P2147
[8]   SELF-IMMOLATIVE ASYMMETRIC SYNTHESIS .3. ALLYLIC REARRANGEMENT OF OPTICALLY-ACTIVE TRICHLOROACETIMIDATE [J].
YAMAMOTO, Y ;
SHIMODA, H ;
ODA, JI ;
INOUYE, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (11) :3247-3249