ENANTIOSELECTIVE SYNTHESIS OF ALLYLAMINES AND PROPARGYLAMINES VIA NUCLEOPHILIC 1,2-ADDITION TO CHIRAL ALDIMINES

被引：27

作者：

ENDERS, D

SCHANKAT, J

机构：

[1] Institute für Oganische Chemie, Rheinisch-Westfälische Technische Hochschule Aachen, D-5100

来源：

HELVETICA CHIMICA ACTA | 1993年 / 76卷 / 01期

关键词：

D O I：

10.1002/hlca.19930760123

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric synthesis of allylamines and propargylamines 5 in high enantiomeric purity (e.e. greater-than-or-equal-to 97%) is described. Key step is the 1,2-addition of organocerium reagents to chiral alpha,beta-unsaturated aldimines 3 to produce secondary amines 4. The chiral auxiliary (S,S)-2 is removed in three steps, affording the title compounds 5, useful bifunctional building blocks and compounds of pharmaceutical interest.

引用

收藏

页码：402 / 406

页数：5

相关论文

共 42 条

[1]

BOCUM A, 1991, TETRAHEDRON LETT, V32, P1367

[2] ASYMMETRIC-SYNTHESIS OF PRIMARY AMINES FROM ALKENES AND CHIRAL CHLORONITROSO SUGAR-DERIVATIVES [J].

BRAUN, H ;

FELBER, H ;

KRESSE, G ;

RITTER, A ;

SCHMIDTCHEN, FP ;

SCHNEIDER, A .

TETRAHEDRON, 1991, 47 (20-21) :3313-3328

[3] ORGANOLITHIUM ADDITION TO ALDEHYDE DIMETHYLHYDRAZONES - A HIGHLY DIASTEREOCONTROLLED SYNTHESIS OF THREO 2-AMINO ALCOHOLS AND (1R,2R)-(-)-NORPSEUDOEPHEDRINE [J].

CLAREMON, DA ;

LUMMA, PK ;

PHILLIPS, BT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) :8265-8266

[4] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[5]

DAUMAS M, 1989, SYNTHESIS-STUTTGART, P64

[6] ORGANOCERIUM ADDITIONS TO SAMP-HYDRAZONES - GENERAL-SYNTHESIS OF CHIRAL AMINES [J].

DENMARK, SE ;

WEBER, T ;

PIOTROWSKI, DW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2224-2225

[7] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED PRIMARY AMINES BY NUCLEOPHILIC-ADDITION TO ALDEHYDE-SAMP HYDRAZONES [J].

ENDERS, D ;

SCHUBERT, H ;

NUBLING, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (12) :1109-1110

[8] ENANTIOSELECTIVE SYNTHESIS OF BETA-SUBSTITUTED PRIMARY AMINES - ALPHA-ALKYLATION REDUCTIVE AMINATION OF ALDEHYDES VIA SAMP-HYDRAZONES [J].

ENDERS, D ;

SCHUBERT, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (05) :365-366

[9]

ENDERS D, 1991, LIEBIGS ANN CHEM, P569, DOI 10.1002/jlac.1991199101103

[10]

ENDERS D, 1993, IN PRESS ANGEW CHEM

← 1 2 3 4 5 →