Diels-alder reactions of N-acyl-2-alkyl(aryl)-5-vinyl-2,3-dihydro-4-pyridones

被引：38

作者：

Comins, DL ^{[1
]}

Kuethe, JT ^{[1
]}

Miller, TM ^{[1
]}

Février, FC ^{[1
]}

Brooks, CA ^{[1
]}

机构：

[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 13期

关键词：

D O I：

10.1021/jo050559n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Readily available N-acyl-5-vinyl-2,3-dihydro-4-pyridones undergo Diels-Alder cyclization with various dienophiles to afford novel octahydroquinolines containing synthetically useful functionality. With dihydropyridone 5 and cis-disubstituted dienophiles, the resulting cycloadducts were obtained as single diastereomers in good to excellent yield. The corresponding reaction of 5 with methyl acrylate, acrylonitrile, and phenyl vinyl sulfone showed modest preference for the endo adducts. The effect of the dihydropyridone C-2 and C-4 substituents on the degree of diastereofacial control was examined. By using this methodology, the core decahydroquinoline skeleton of gephyrotoxin was prepared in a stereocontrolled fashion. Interesting reactivity was observed with certain dienophiles leading to ring-opening of the initially formed cycloadducts. This tandem reaction provides a route to uniquely substituted beta-aminoketones, alcohols, and unnatural amino acids.

引用

页码：5221 / 5234

页数：14

共 71 条

[31]

HOLMES AB, 1992, J CHEM SOC P1, V9, P1089

[32]

HOLMES AB, 1993, J CHEM SOC P1, V5, P633

[33] Total synthesis of (+)-streptazolin [J].

Huang, SL ;

Comins, DL .

CHEMICAL COMMUNICATIONS, 2000, (07) :569-570

[34] DIISOBUTYLALUMINUM "2,6-DI-TERT-BUTYL-4-METHYLPHENOXIDE - NOVEL STEREOSELECTIVE REDUCING AGENT FOR PROSTAGLANDIN SYNTHESIS [J].

IGUCHI, S ;

NAKAI, H ;

HAYASHI, M ;

YAMAMOTO, H ;

MARUOKA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (10) :3033-3041

[35] A NEW APPROACH TO GEPHYROTOXIN [J].

ITO, Y ;

NAKAJO, E ;

NAKATSUKA, M ;

SAEGUSA, T .

TETRAHEDRON LETTERS, 1983, 24 (28) :2881-2884

[36]

JESSUP PJ, 1988, ORG SYNTH COLL, V6, P95

[37] Asymmetric synthesis of chiral, nonracemic trifluoromethyl-substituted piperidines and decahydroquinolines [J].

Jiang, JL ;

DeVita, RJ ;

Doss, GA ;

Goulet, MT ;

Wyvratt, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (03) :593-594

[38]

KALAUS G, 1985, HETEROCYCLES, V23, P2783

[39] STUDIES IN BIOMIMETIC ALKALOID SYNTHESES .4. ALTERNATIVE ROUTE TO SECODINE INTERMEDIATES PROVIDING SYNTHESES OF MINOVINE, VINCADIFFORMINE, ERVINCEINE, AND N(A)-METHYLERVINCEINE [J].

KUEHNE, ME ;

HUEBNER, JA ;

MATSKO, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2477-2480

[40] Tandem Diels-Alder cyclization/aromatization reactions of 5-vinyl-1-acyl-2-aryl-2,3-dihydro-4-pyridones [J].

Kuethe, JT ;

Comins, DL .

TETRAHEDRON LETTERS, 2003, 44 (22) :4179-4182

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