NEW SYNTHETIC METHODOLOGY FOR THE SYNTHESIS OF 7-SUBSTITUTED TETRAHYDROAZEPIN-2-ONES

被引：17
作者：
EVANS, PA
HOLMES, AB
RUSSELL, K
机构：
[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CTR MOLEC RECOGNIT,CAMBRIDGE CB2 1EW,ENGLAND
[2] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 23期
关键词：
D O I：
10.1039/p19940003397
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Claisen rearrangement of the vinyl substituted ketene aminals 2 (R=CH(2)CHMe(2), CH(2)OSiBu(t)Me(2)) which were generated in situ by selenoxide elimination of the aminal precursors 3 in the presence of 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) furnished the enantiomerically pure 7-substituted tetrahydroazepin-2-ones 1.
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页码：3397 / 3409
页数：13
相关论文
共 44 条
[21]   PREPARATION AND SYNTHETIC UTILITY OF TERT-BUTYLDIPHENYLSILYL ETHERS [J].
HANESSIAN, S ;
LAVALLEE, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (19) :2975-2977
[22]   STEREOSELECTIVE SYNTHESIS OF (+/-)-INDOLIZIDINES 167B, 205A, AND 207A - ENANTIOSELECTIVE SYNTHESIS OF (-)-INDOLIZIDINE 209B [J].
HOLMES, AB ;
SMITH, AL ;
WILLIAMS, SF ;
HUGHES, LR ;
LIDERT, Z ;
SWITHENBANK, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1393-1405
[23]  
ITO A, 1975, CHEM PHARM BULL, V23, P3081
[24]   CLAISEN-BASED STRATEGY FOR THE DENOVO CONSTRUCTION OF BASMANE DITERPENES - ENANTIOSPECIFIC SYNTHESIS OF (+)-7,8-EPOXY-2-BASMEN-6-ONE [J].
KANG, HJ ;
PAQUETTE, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3252-3253
[25]   UNUSUAL RING EXPANSION OBSERVED DURING THE DAKIN-WEST REACTION OF TETRAHYDROISOQUINOLINE-1-CARBOXYLIC ACIDS USING TRIFLUOROACETIC-ANHYDRIDE - AN EXPEDIENT SYNTHESIS OF 3-BENZAZEPINE DERIVATIVES BEARING A TRIFLUOROMETHYL GROUP [J].
KAWASE, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (15) :1076-1077
[26]   GENERAL-APPROACH TO ANNULATED 4-CYCLOOCTENONES BY ALIPHATIC CLAISEN REARRANGEMENT - STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-PRECAPNELLADIENE [J].
KINNEY, WA ;
COGHLAN, MJ ;
PAQUETTE, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7352-7360
[27]   OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].
MANCUSO, AJ ;
HUANG, SL ;
SWERN, D .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482
[28]  
MOORE JA, 1984, COMPREHENSIVE HETERO, V7, P653
[29]  
OCCHIATO EG, 1993, GAZZ CHIM ITAL, V123, P425
[30]  
OVERMAN LE, 1992, SYNLETT, P995
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