Stereoselective α-amidoalkylation reactions of phenylglycinol-derived bicyclic lactams

被引:25
作者
Amat, M [1 ]
Escolano, C [1 ]
Llor, N [1 ]
Huguet, M [1 ]
Pérez, M [1 ]
Bosch, J [1 ]
机构
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
关键词
D O I
10.1016/S0957-4166(03)00250-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The stereochemical outcome of alpha-amidoalkylation reactions from the chiral non-racemic bicyclic lactams trans-1 and cis-1 using indole, allyttrimethylsilane, higher order organocuprates, TMSCN, and Grignard reagents is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1679 / 1683
页数:5
相关论文
共 24 条
[1]   Enantioselective syntheses of the indole alkaloid (+)-R-decarbomethoxytetrahydrosecodine and its enantiomer [J].
Amat, M ;
Pshenichnyi, G ;
Bosch, J ;
Molins, E ;
Miravitlles, C .
TETRAHEDRON-ASYMMETRY, 1996, 7 (11) :3091-3094
[2]   Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam [J].
Amat, M ;
Llor, N ;
Hidalgo, J ;
Escolano, C ;
Bosch, J .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1919-1928
[3]   On the configuration of (3R,8aS)-5-oxo-3-pheny-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine [J].
Amat, M ;
Llor, N ;
Escolano, C ;
Huguet, M ;
Pérez, M ;
Molins, E ;
Bosch, J .
TETRAHEDRON-ASYMMETRY, 2003, 14 (03) :293-295
[4]   Enantioselective synthesis of 2-arylpiperidines from chiral lactams.: A concise synthesis of (-)-anabasine [J].
Amat, M ;
Cantó, M ;
Llor, N ;
Bosch, J .
CHEMICAL COMMUNICATIONS, 2002, (05) :526-527
[5]   Stereodivergent synthesis of enantiopure cis- and trans-3-ethyl-4-piperidineacetates [J].
Amat, M ;
Pérez, M ;
Llor, N ;
Bosch, J .
ORGANIC LETTERS, 2002, 4 (16) :2787-2790
[6]   Conjugate addition of organocuprates to chiral bicyclic δ-lactams.: Enantioselective synthesis of cis-3,4-disubstituted and 3,4,5-trisubstituted piperidines [J].
Amat, M ;
Pérez, M ;
Llor, N ;
Bosch, J ;
Lago, E ;
Molins, E .
ORGANIC LETTERS, 2001, 3 (04) :611-614
[7]   CHIRAL PRECURSORS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE PIPERIDINES - TOTAL SYNTHESIS OF (R)-(-)-CONIINE [J].
AMAT, M ;
LLOR, N ;
BOSCH, J .
TETRAHEDRON LETTERS, 1994, 35 (14) :2223-2226
[8]   Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine [J].
Amat, M ;
Bosch, J ;
Hidalgo, J ;
Cantó, M ;
Pérez, M ;
Llor, N ;
Molins, E ;
Miravitlles, C ;
Orozco, M ;
Luque, J .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3074-3084
[9]   Preparation of enantiopure 6-(3-indolyl)-2-piperidones and conjugate additions to a 3,4-didehydro derivative [J].
Amat, M ;
Llor, N ;
Bosch, J ;
Solans, X .
TETRAHEDRON, 1997, 53 (02) :719-730
[10]   ASYMMETRIC-SYNTHESIS OF GAMMA,GAMMA-DIALKYL-GAMMA-AMINOBUTYRIC ACID ANALOGS AND 2,2-DISUBSTITUTED PYRROLIDINES - CONTROL OF STEREOCHEMISTRY IN AMINAL RING-OPENING BY VARYING THE EXTENT OF ALLYLIC 1,3-STRAIN [J].
BURGESS, LE ;
MEYERS, AI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9858-9859