ASYMMETRIC ADDITION OF BUTYLLITHIUM TO N-METALLO IMINES OF BENZALDEHYDE

被引：42

作者：

ITSUNO, S

SASAKI, M

KURODA, S

ITO, K

机构：

[1] Department of Materials Science, Toyohashi University of Technology, Toyohashi, 441, Tempaku-cho

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 07期

关键词：

D O I：

10.1016/0957-4166(95)00184-Q

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

N-Metallo imines derived from benzaldehyde such as N-aluminium imine, N-boryl imine and N-silyl inline,were asymmetrically alkylated with butyllithium iri the presence of chiral ligands including (-)-sparteine and proline-derived amino alcohols to give optically active 1-phenylpentyl-1-amine in up to 74 % enantiomeric excess. Polymer-supported chiral ligands were also used for the asymmetric addition.

引用

页码：1507 / 1510

页数：4

共 33 条

[1] REACTIVITY AND DIASTEREOSELECTIVITY OF GRIGNARD-REAGENTS TOWARD THE HYDRAZONE FUNCTIONALITY IN TOLUENE SOLVENT
ALEXAKIS, A
LENSEN, N
TRANCHIER, JP
MANGENEY, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) : 4563 - 4565
[2] PREPARATION OF PRIMARY AMINES VIA N-DIISOBUTYLALUMINUM IMINES
ANDREOLI, P
BILLI, L
CAINELLI, G
PANUNZIO, M
MARTELLI, G
SPUNTA, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) : 4199 - 4200
[3] ORGANOLITHIUM ADDITION TO ALDEHYDE DIMETHYLHYDRAZONES - A HIGHLY DIASTEREOCONTROLLED SYNTHESIS OF THREO 2-AMINO ALCOHOLS AND (1R,2R)-(-)-NORPSEUDOEPHEDRINE
CLAREMON, DA
LUMMA, PK
PHILLIPS, BT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) : 8265 - 8266
[4] DIASTEREOSELECTIVE ADDITION OF LITHIATED N,N-DIETHYL-ORTHO-TOLUAMIDE TO CHIRAL ISOPROPYLIDINE GLYCERALDEHYDE IMINES - ASYMMETRIC-SYNTHESIS OF 3-SUBSTITUTED 3,4-DIHYDRO-1(2H)-ISOQUINOLONES
CLARK, RD
JAHANGIR
SOUCHET, M
KERN, JR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) : 930 - 931
[5] ASYMMETRIC ADDITION OF ORGANOLITHIUM REAGENTS TO IMINES
DENMARK, SE
NAKAJIMA, N
NICAISE, OJC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8797 - 8798
[6] ORGANOCERIUM ADDITIONS TO SAMP-HYDRAZONES - GENERAL-SYNTHESIS OF CHIRAL AMINES
DENMARK, SE
WEBER, T
PIOTROWSKI, DW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) : 2224 - 2225
[7] ENDERS D, 1986, ANGEW CHEM INT EDIT, V25, P2224
[8] HATANAKA SK, 1992, J CHEM SOC CHEM COMM, P1097
[9] CHIRAL LITHIUM-1-OXYALKANIDES BY ASYMMETRIC DEPROTONATION - ENANTIOSELECTIVE SYNTHESIS OF 2-HYDROXYALKANOIC ACIDS AND SECONDARY ALKANOLS
HOPPE, D
HINTZE, F
TEBBEN, P
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (12): : 1422 - 1424
[10] ASYMMETRIC 1,2-ADDITION OF ORGANOLITHIUMS TO ALDIMINES CATALYZED BY CHIRAL LIGAND
INOUE, I
SHINDO, M
KOGA, K
TOMIOKA, K
[J]. TETRAHEDRON, 1994, 50 (15) : 4429 - 4438

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