Alkylation of phenylglycinol-derived bicyclic lactams.: Enantioselective synthesis of 3-alkylpiperidines

被引:14
作者
Amat, M [1 ]
Escolano, C [1 ]
Llor, NR [1 ]
Lozano, O [1 ]
Gómez-Esqué, A [1 ]
Griera, R [1 ]
Bosch, J [1 ]
机构
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, Av Joan XXIII S-N, E-08028 Barcelona, Spain
关键词
chiral bicyclic lactams; phenylglycinol; alkylation; enantioselective synthesis;
D O I
10.3998/ark.5550190.0006.912
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereochemical outcome of the alkylation of simple phenylglycinol-derived bicyclic lactams has been studied. The method provides a simple and concise route to 3-alkylpiperidines in both enantiomeric series. The synthesis of (+)-R-decarbomethoxytetrahydrosecodine, an indole alkaloid embodying a 3-ethylpiperidine moiety, is reported.
引用
收藏
页码:115 / 123
页数:9
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