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

被引:16
作者
ANASTASIOU, D
JACKSON, WR
机构
[1] Department of Chemistry, Monash University, Clayton
关键词
D O I
10.1016/0022-328X(91)80065-R
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Rhodium-catalysed reactions of 5-aminopent-1-enes with carbon monoxide and hydrogen give 2-piperidinone derivatives in high yields under mild conditions. Reaction of allylamine under similar conditions gave exclusively 2-pyrrolidone in high yield and reactions of 4-aminobut-1-enes gave mixtures of 2-piperidinones and 2-pyrrolidinones. The role of the hydrogen in these reactions is discussed.
引用
收藏
页码:399 / 410
页数:12
相关论文
共 34 条
[1]   PLATINUM-PROMOTED CYCLIZATION REACTIONS OF AMINO OLEFINS .2. REGIOSELECTIVITY AND STEREOSELECTIVITY IN THE CYCLIZATION REACTIONS OF C-METHYL SUBSTITUTED PENT-4-ENYLAMINES [J].
AMBUEHL, J ;
PREGOSIN, PS ;
VENANZI, LM ;
CONSIGLIO, G ;
BACHECHI, F ;
ZAMBONELLI, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 181 (01) :255-269
[2]  
ANASTASIOU D, IN PRESS AUST J CHEM
[3]   RHODIUM-CATALYZED HYDROFORMYLATIONS OF UNSATURATED NITROGEN-HETEROCYCLES - REGIOSELECTIVITY AND STEREOSELECTIVITY IN THE SYNTHESIS OF TROPANE AND PIPERIDINE CARBOXYALDEHYDES [J].
BANACH, D ;
EVANS, GO ;
MCINTYRE, DG ;
PREDMORE, T ;
RICHMOND, MG ;
SUPPLE, JH ;
STEWART, RP .
JOURNAL OF MOLECULAR CATALYSIS, 1985, 31 (01) :15-37
[4]   PREPARATION OF OLEFINIC DERIVATIVES OF PHTHALIMIDE AND THEIR USE AS PRECURSORS FOR HOMOALLYLIC AMINES [J].
BERGMANN, ED ;
MIGRON, Y .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1976, 8 (02) :75-80
[5]   LIMITED SCOPE OF AZABICYCLOHEXANE SYNTHESIS FROM DELTA,EPSILON-UNSATURATED AMINES [J].
BLACK, DSC ;
DOYLE, JE .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (10) :2247-2257
[6]   THERMAL-DECOMPOSITION OF QUATERNARY AMMONIUM HYDROXIDES .5. IMPORTANCE OF CONFORMATIONAL FACTORS IN BETA-ELIMINATIONS FROM QUATERNARY HYDROXIDES DERIVED FROM PIPERIDINES, MORPHOLINES, AND DECAHYDROQUINOLINES [J].
BOOTH, H ;
BOSTOCK, AH ;
FRANKLIN, NC ;
GRIFFITHS, DV ;
LITTLE, JH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (09) :899-907
[7]   H-1 AND C-13 NMR-STUDY ON SOME SUBSTITUTED AZOLIDINE DERIVATIVES [J].
CERIONI, G ;
CRISTIANI, F ;
DEVILLANOVA, FA ;
DIAZ, A ;
VERANI, G .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1983, 39 (10) :929-932
[8]  
CONSIGLIO G, 1982, TOP CURR CHEM, V105, P77
[9]   THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .34. REGIOSELECTION IN THE HYDROFORMYLATION OF SILYLALKENES [J].
DOYLE, MM ;
JACKSON, WR ;
PERLMUTTER, P .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (11) :1907-1918
[10]   THE STEREOCHEMISTRY OF ORGANO-METALLIC COMPOUNDS .21. ASYMMETRIC ADDITION OF HYDROGEN-CYANIDE TO ALKENES CATALYZED BY ZEROVALENT METAL-COMPOUNDS [J].
ELMES, PS ;
JACKSON, WR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (10) :2041-2051