Highly enantioselective dynamic kinetic resolution and desymmetrization processes by cyclocondensation of chiral aminoalcohols with racemic or prochiral δ-oxoacid derivatives

被引:31
作者
Amat, M [1 ]
Bassas, O
Pericàs, MA
Pastó, M
Bosch, J
机构
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
[2] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain
关键词
D O I
10.1039/b413937b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cyclocondensation reactions of aminoalcohols 7 and 8 with racemic or prochiral delta-oxoacid derivatives provide polysubstituted lactams with high enantioselectivity in a process that involves dynamic kinetic resolution and/or desymmetrization of enantiotopic or diastereotopic ester groups.
引用
收藏
页码:1327 / 1329
页数:3
相关论文
共 18 条
[1]   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
[2]  
Amat M, 2002, ANGEW CHEM INT EDIT, V41, P335, DOI 10.1002/1521-3773(20020118)41:2<335::AID-ANIE335>3.0.CO
[3]  
2-Y
[4]   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
[5]   Asymmetric routes to substituted piperidines [J].
Bailey, PD ;
Millwood, PA ;
Smith, PD .
CHEMICAL COMMUNICATIONS, 1998, (06) :633-640
[6]   Synthesis of piperidines [J].
Buffat, MGP .
TETRAHEDRON, 2004, 60 (08) :1701-1729
[7]   A chemo-enzymatic approach to some indole and quinolizidine alkaloids from Cs-symmetric precursors [J].
Danieli, B ;
Lesma, G ;
Passarella, D ;
Silvani, A .
CURRENT ORGANIC CHEMISTRY, 2000, 4 (02) :231-261
[8]   Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions [J].
Groaning, MD ;
Meyers, AI .
TETRAHEDRON, 2000, 56 (51) :9843-9873
[9]  
Laschat S, 2000, SYNTHESIS-STUTTGART, P1781
[10]   ASYMMETRIC SYNTHESIS OF R AND S ALPHA-ALKYLALKANOIC ACIDS FROM METALATION AND ALKYLATION OF CHIRAL 2-OXAZOLINES [J].
MEYERS, AI ;
KNAUS, G ;
KAMATA, K ;
FORD, ME .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (02) :567-576