Metallic salt promoted radical cyclization of β-keto carboxamides and their corresponding β-enamino carboxamides

被引：41

作者：

Cossy, J ^{[1
]}

Bouzide, A ^{[1
]}

Leblanc, C ^{[1
]}

机构：

[1] Ecole Super Phys & Chim Ind, Chim Organ Lab, CNRS, F-75231 Paris 05, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 22期

关键词：

D O I：

10.1021/jo000084u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted lactams and spirolactams were obtained by Mn(III)-induced radical cyclization of unsaturated beta -keto carboxamides. Treatment of the corresponding tertiary enamines under similar reaction conditions and in the presence of K2CO3 afforded the same cyclized products but with inversion of diastereoselectivity. The oxidation of optically pure secondary enamines leads to diastereomeric spirolactams in an approximately 3:1 ratio.

引用

页码：7257 / 7265

页数：9

共 62 条

[1] ELECTROCHEMICAL EVIDENCE FOR INTRAMOLECULAR REACTIONS OF THE ELECTROGENERATED CATION - RADICALS OF SOME AMIDOENAMINES [J].

AUDEBERT, P ;

BEKOLO, H ;

COSSY, J ;

BOUZIDE, A .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1995, 389 (1-2) :215-218

[2] PREPARATION OF SMALL RING CARBOCYCLES VIA INTRAMOLECULAR OXIDATIVE COUPLING OF BISENOLATES DERIVED FROM ALPHA,OMEGA-DIESTERS [J].

BABLER, JH ;

SARUSSI, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3462-3464

[3] ALKENES FROM ACIDS BY OXIDATIVE DECARBOXYLATION [J].

BACHA, JD ;

KOCHI, JK .

TETRAHEDRON, 1968, 24 (05) :2215-&

[4] COBALT(II) CATALYZED REACTION OF ALKENES WITH ALIPHATIC-ALDEHYDES AND MOLECULAR-OXYGEN - SCOPE AND MECHANISM [J].

BHATIA, S ;

PUNNIYAMURTHY, T ;

BHATIA, B ;

IQBAL, J .

TETRAHEDRON, 1993, 49 (27) :6101-6122

[5]

CARDILLO B, 1995, SYNLETT, P1159

[6] ELECTROCHEMICAL OXIDATION OF ENAMINES IN THE PRESENCE OF ORGANIC-ANIONS [J].

CHIBA, T ;

OKIMOTO, M ;

NAGAI, H ;

TAKATA, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (20) :3519-3523

[7]

CHRETIEN A, 1936, B SOC CHIM FR, V3, P2385

[8] OXIDATIVE CYCLIZATION OF DICARBOXYLATE DIENOLATES AS A NEW CYCLIZATION METHOD [J].

CHUNG, SK ;

DUNN, LB .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1125-1127

[9]

COREY EJ, 1987, CHEM LETT, P225

[10]

COSSY J, 1994, B SOC CHIM FR, V131, P723

← 1 2 3 4 5 6 7 →