SYNTHESIS OF PYRROLIDINES AND PYRROLIDINONES BY THE RHODIUM COMPLEX CATALYZED CYCLIZATION OF UNSATURATED AMINES

被引：44

作者：

ZHOU, JQ ^{[1
]}

ALPER, H ^{[1
]}

机构：

[1] UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 6N5,ONTARIO,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 12期

关键词：

D O I：

10.1021/jo00038a019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Allylic arylamines react with carbon monoxide, sodium borohydride, 2-propanol, and catalytic amounts of the zwitterionic complex eta-6-C6H6BPh3-Rh(COD)+ (1), to form pyrrolidines as the main products in most cases. Pyrrolidinones result from N-allylic alkylamines. An alternate route to the lactams from N-allylic alkylamines involves synthesis gas instead of CO/NaBH4, together with the dual catalytic system 1/[Ru(CO)3Cl2]2. Complementary to the N-allylic arylamine route to pyrrolidines with NaBH4 and 1 is the use of synthesis gas, 1, and 1,4-bis(diphenylphosphino)butane.

引用

页码：3328 / 3331

页数：4

共 20 条

[1] KINETIC AND EQUILIBRIUM PROTONATION OF SOME ALKYLATED 1,8-DIAMINONAPHTHALENE MONOCATIONS TO FORM DICATIONS - CARBON VERSUS NITROGEN PROTONATION [J].

ALDER, RW ;

BRYCE, MR ;

GOODE, NC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (04) :477-483

[2] ZWITTERIONIC RHODIUM COMPLEXES AS CATALYSTS FOR THE HYDROFORMYLATION OF OLEFINS [J].

AMER, I ;

ALPER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3674-3676

[3] THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .36. RHODIUM-CATALYZED REACTIONS OF UNSATURATED AMINES WITH HYDROGEN AND CARBON-MONOXIDE - A NEW SYNTHESIS OF 2-PIPERIDINONES [J].

ANASTASIOU, D ;

JACKSON, WR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 413 (1-3) :399-410

[4]

ANASTASSIOU D, 1990, THESIS MONASH U

[5] NEW METHODS IN PREPARATIVE ORGANIC CHEMISTRY .6. RING CLOSURES WITH CARBON MONOXIDE [J].

FALBE, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (05) :435-+

[6] SYNTHESEN MIT KOHLENMONOXYD .6. LACTAME DURCH RINGSCHLUSSREAKTION UNGESATTIGTER AMINE MIT KOHLENMONOXYD [J].

FALBE, J ;

KORTE, F .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (06) :1928-&

[7]

FALBE J, 1965, TETRAHEDRON LETT, P2677

[8]

Falbe J., 1980, CARBON MONOXIDE ORGA

[9] SYNTHETIC ZEOLITES AS CATALYSTS FOR RING CONVERSION OF GAMMA-BUTYROLACTONE INTO 1-SUBSTITUTED 2-PYRROLIDINONES [J].

HATADA, K ;

ONO, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (10) :2517-2521

[10] DIRECT N-ALLYLATION OF AMIDES WITH 2-ALLYLISOUREA CATALYZED BY PALLADIUM(O) [J].

INOUE, Y ;

TAGUCHI, M ;

HASHIMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (09) :2721-2722

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