A new route to ene carbamates, precursors to benzoindolizinones through sequential asymmetric hydrogenation and cyclization

被引：21

作者：

Couture, A ^{[1
]}

Deniau, E

Lebrun, S

Grandclaudon, P

Carpentier, JF

机构：

[1] Univ Sci & Tech Lille Flandres Artois, CNRS URA 351, Chim Organ Phys Lab, F-59655 Villeneuve Dascq, France

[2] Univ Sci & Tech Lille Flandres Artois, CNRS URA 402, Lab Chim Organ Appl, F-59655 Villeneuve Dascq, France

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 08期

关键词：

D O I：

10.1039/a709053f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New pyrrolidine-based ene carbamates have been efficiently synthesized and the first example of asymmetric hydrogenation of this kind of substrate is reported, leading to the preparation of 2-arylmethylpyrrolidine precursors to benzoindolizinones in high yields and enantioselectivities up to 57%.

引用

收藏

页码：1403 / 1407

页数：5

相关论文

共 22 条

[1] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].

Beak, P ;

Basu, A ;

Gallagher, DJ ;

Park, YS ;

Thayumanavan, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560

[2] Base-induced cyclization of trimethoxy-o-aroyldiphenylphosphoryl methylbenzamide: A formal synthesis of (+/-)cherylline and (+/-)cherylline dimethylether [J].

Couture, A ;

Deniau, E ;

Woisel, P ;

Grandclaudon, P ;

Carpentier, JF .

TETRAHEDRON LETTERS, 1996, 37 (21) :3697-3700

[3] Dramatically different photochemical behaviour of 1-aroyl-2-methylene piperidine and pyrrolidine derivatives. An expeditious synthesis of ruspolinone [J].

Couture, A ;

Deniau, E ;

Grandclaudon, P ;

Lebrun, S .

TETRAHEDRON LETTERS, 1996, 37 (43) :7749-7752

[4] Asymmetric induction alpha to nitrogen in pyrrolidines and piperidines via radical chemistry [J].

Ewin, RA ;

Jones, K ;

Newton, CG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (11) :1107-1111

[5] 1-magnesiotetrahydroisoquinolyloxazolines as chiral nucleophiles in stereoselective additions to aldehydes: Auxiliary optimization, asymmetric synthesis of (+)-corlumine, (+)-bicuculline, (+)-egenine, and (+)-corytensine, and preliminary C-13 NMR studies of 1-lithio- and 1-magnesiotetrahydroisoquinolyloxazolines [J].

Gawley, RE ;

Zhang, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8103-8112

[6] ASYMMETRIC-SYNTHESIS OF BENZOQUINOLIZIDINES - A FORMAL SYNTHESIS OF (-)-EMETINE [J].

GUILES, JW ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6873-6878

[7] NEW EFFICIENT METHODS FOR THE SYNTHESIS AND INSITU PREPARATION OF RUTHENIUM(II) COMPLEXES OF ATROPISOMERIC DIPHOSPHINES AND THEIR APPLICATION IN ASYMMETRIC CATALYTIC HYDROGENATIONS [J].

HEISER, B ;

BROGER, EA ;

CRAMERI, Y .

TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :51-62

[8]

Highsmith T.K., 1991, ADV HETEROCYCLIC NAT, VI, P95

[9] GENERAL ASYMMETRIC-SYNTHESIS OF ISOQUINOLINE ALKALOIDS - ENANTIOSELECTIVE HYDROGENATION OF ENAMIDES CATALYZED BY BINAP-RUTHENIUM(II) COMPLEXES [J].

KITAMURA, M ;

HSIAO, Y ;

OHTA, M ;

TSUKAMOTO, M ;

OHTA, T ;

TAKAYA, H ;

NOYORI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :297-310

[10]

LIENARD P, 1991, TETRAHEDRON LETT, V32, P2489