HIGHLY STEREOSELECTIVE ADDITION OF ALKYLCOPPER REAGENTS TO N-ACYLIMINIUM IONS - ENANTIOSELECTIVE SYNTHESIS OF TRANS-2-BUTYL-5-HEPTYLPYRROLIDINE

被引:56
作者
SKRINJAR, M [1 ]
WISTRAND, LG [1 ]
机构
[1] UNIV LUND,CTR CHEM,POB 124,S-22100 LUND,SWEDEN
关键词
D O I
10.1016/S0040-4039(00)88878-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Addition of RCu, BF3 to the electrochemically prepared α-methoxy proline ester 1 has been shown to be highly trans (≥96%) selective. This reaction has been developed into an enantioselective synthesis of the ant trail feromone trans-2-butyl-5-heptylpyrrolidine. © 1990.
引用
收藏
页码:1775 / 1778
页数:4
相关论文
共 16 条
[1]   ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING [J].
ARSENIYADIS, S ;
HUANG, PQ ;
PIVETEAU, D ;
HUSSON, HP .
TETRAHEDRON, 1988, 44 (09) :2457-2470
[2]   ASYMMETRIC-SYNTHESIS .13. SYNTHESIS OF 2-ALKYLPYRROLIDINES - TOWARDS AZABICYCLIC SYSTEMS [J].
ARSENIYADIS, S ;
HUANG, PQ ;
HUSSON, HP .
TETRAHEDRON LETTERS, 1988, 29 (06) :631-634
[3]   ENANTIOSELECTIVE SYNTHESIS OF 7 PYRROLIZIDINE DIOLS FROM A SINGLE PRECURSOR [J].
CHAMBERLIN, AR ;
CHUNG, JYL .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4425-4431
[4]   TRIMETHYLSILYL IODIDE AS A PEPTIDE DEBLOCKING AGENT [J].
LOTT, RS ;
CHAUHAN, VS ;
STAMMER, CH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (11) :495-496
[5]  
LUDWIG C, IN PRESS
[6]   1-FORMYL-5-METHOXYPROLINE METHYL-ESTER - ELECTROCHEMICAL PREPARATION AND USE AS AMIDOALKYLATION REAGENT [J].
MALMBERG, M ;
NYBERG, K .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (01) :85-93
[7]   ENANTIOMERICALLY PURE PYRROLIDINE DERIVATIVES FROM TRANS-4-HYDROXY-L-PROLINE BY ELECTROCHEMICAL OXIDATIVE DECARBOXYLATION AND TITANIUM-TETRACHLORIDE-MEDIATED REACTION WITH NUCLEOPHILES [J].
RENAUD, P ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1986, 69 (07) :1704-1710
[8]   ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - CHIROSPECIFIC SYNTHESES OF THE 5-BUTYL-2-HEPTYLPYRROLIDINES FROM GLUTAMIC-ACID [J].
SHIOSAKI, K ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1229-1239
[9]   ELECTROORGANIC CHEM .96. SYNTHESIS OF OPTICALLY-ACTIVE PIPERIDINE AND PYRROLIDINE ALKALOIDS FROM L-LYSINE, L-ORNITHINE, OR L-PROLINE USING ANODIC-OXIDATION AS KEY STEPS [J].
SHONO, T ;
MATSUMURA, Y ;
TSUBATA, K ;
UCHIDA, K .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (13) :2590-2592
[10]   ELECTROORGANIC CHEMISTRY IN ORGANIC-SYNTHESIS [J].
SHONO, T .
TETRAHEDRON, 1984, 40 (05) :811-850