TRANSITION-METAL CATALYZED RADICAL CYCLIZATION - NEW PREPARATIVE ROUTE TO GAMMA-LACTAMS FROM ALLYLIC ALCOHOLS VIA THE [3.3]-SIGMATROPIC REARRANGEMENT OF ALLYLIC TRICHLOROACETIMIDATES AND THE SUBSEQUENT RUTHENIUM-CATALYZED CYCLIZATION OF N-ALLYLTRICHLOROACETAMIDES

被引：106

作者：

NAGASHIMA, H ^{[1
]}

WAKAMATSU, H ^{[1
]}

OZAKI, N ^{[1
]}

ISHII, T ^{[1
]}

WATANABE, M ^{[1
]}

TAJIMA, T ^{[1
]}

ITOH, K ^{[1
]}

机构：

[1] TOYOHASHI UNIV TECHNOL,DEPT MAT SCI,TOYOHASHI,AICHI 441,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 06期

关键词：

D O I：

10.1021/jo00032a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated gamma-lactams from allylic alcohols. No delta-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.

引用

页码：1682 / 1689

页数：8

共 43 条

[1] CHLORINE-ACTIVATION BY REDOX-TRANSFER .3. ABNORMAL ADDITION OF CHLOROFORM TO OLEFINS [J].

ASSCHER, M ;

VOFSI, D .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (AUG) :3921-&

[2] CHLORINE ACTIVATION BY REDOX-TRANSFER .1. REACTION BETWEEN ALIPHATIC AMINES AND CARBON TETRACHLORIDE [J].

ASSCHER, M ;

VOFSI, D .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JUN) :2261-&

[3] CHLORINE ACTIVATION BY REDOX TRANSFER .2. ADDITION OF CARBON TETRACHLORIDE TO OLEFINS [J].

ASSCHER, M ;

VOFSI, D .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (MAR) :1887-&

[4] RADICAL CYCLIZATIONS OF ALPHA-FLUORO-ALPHA-IODO AND ALPHA-IODO ESTERS AND AMIDES [J].

BARTH, F ;

OYANG, C .

TETRAHEDRON LETTERS, 1990, 31 (08) :1121-1124

[5] FORMATION OF LINEAR TRIQUINANES BY SERIAL HOMOLYTIC CYCLIZATION [J].

BECKWITH, ALJ ;

ROBERTS, DH ;

SCHIESSER, CH ;

WALLNER, A .

TETRAHEDRON LETTERS, 1985, 26 (28) :3349-3352

[6] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].

BECKWITH, ALJ ;

SCHIESSER, CH .

TETRAHEDRON, 1985, 41 (19) :3925-3941

[7]

BRESLOW R, 1968, TETRAHEDRON LETT, P1837

[8]

BRESLOW R, 1966, TETRAHEDRON LETT, P4717

[9] RADICAL CYCLIZATIONS OF PROPARGYL BROMOAMIDES AND PROPARGYL BROMOESTERS - NEW ROUTES TO TETRAMIC ACIDS, PYRROLINONES, TETRONIC ACIDS AND BUTENOLIDES [J].

CLOUGH, JM ;

PATTENDEN, G ;

WIGHT, PG .

TETRAHEDRON LETTERS, 1989, 30 (52) :7469-7472

[10] EFFECTS OF TEMPERATURE ON ATOM TRANSFER CYCLIZATION REACTIONS OF ALLYLIC ALPHA-IODO ESTERS AND AMIDES [J].

CURRAN, DP ;

TAMINE, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2746-2750

← 1 2 3 4 5 →