Highly diastereoselective and enantioselective carbon-carbon bond formations in conjugate additions of lithiated N-boc allylamines to nitroalkenes:: Enantioselective synthesis of 3,4-and 3,4,5-substituted piperidines including (-)-paroxetine

被引:120
作者
Johnson, TA [1 ]
Curtis, MD [1 ]
Beak, P [1 ]
机构
[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
关键词
D O I
10.1021/ja005748w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:1004 / 1005
页数:2
相关论文
共 16 条
[1]   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
[2]   Asymmetric routes to substituted piperidines [J].
Bailey, PD ;
Millwood, PA ;
Smith, PD .
CHEMICAL COMMUNICATIONS, 1998, (06) :633-640
[3]   APPROACHES TO CARBOCYCLIC ANALOGS OF THE POTENT NEURAMINIDASE INHIBITOR 4-GUANIDINO-NEU5AC2EN - X-RAY MOLECULAR-STRUCTURE OF N-[(1S,2S,6R)-2-AZIDO-6-BENZYLOXYMETHYL-4-FORMYLCYCLOHEX-3-ENYL]ACETAMIDE [J].
CHANDLER, M ;
CONROY, R ;
COOPER, AWJ ;
LAMONT, RB ;
SCICINSKI, JJ ;
SMART, JE ;
STORER, R ;
WEIR, NG ;
WILSON, RD ;
WYATT, PG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (09) :1189-1197
[4]   Asymmetric carbon-carbon bond formation in Michael reactions: Conjugate addition reactions of configurationally stable benzylic and allylic organolithium species [J].
Curtis, MD ;
Beak, P .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :2996-2997
[5]   Alkaloid synthesis using chiral δ-amino β-ketoesters:: A stereoselective synthesis of (-)-lasubine II [J].
Davis, FA ;
Chao, B .
ORGANIC LETTERS, 2000, 2 (17) :2623-2625
[6]   Synthesis of enantiomerically pure cis-2,4-disubstituted piperidines:: extension of chiral homoenolate alkylations toward the preparation of nitrogen heterocycles [J].
Dwyer, MP ;
Lamar, JE ;
Meyers, AI .
TETRAHEDRON LETTERS, 1999, 40 (51) :8965-8968
[7]  
Elbein A. D., 1987, ALKALOIDS CHEM BIOL, V5, P1
[8]  
Guilloteau-Bertin B, 2000, EUR J ORG CHEM, V2000, P1391
[9]   Asymmetric Diels-Alder reactions of 2-azadienes catalyzed by a chiral copper(II) complex. A general route to enantiomerically pure piperidones [J].
Jnoff, E ;
Ghosez, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2617-2618
[10]   A simple and stereospecfic route to 2,6-disubstituted 4-hydroxypiperidines. Synthesis of dendrobate alkaloid (+)-241D and formal synthesis of (-)-indolizidine 167B [J].
Ma, DW ;
Sun, HY .
ORGANIC LETTERS, 2000, 2 (16) :2503-2505