NOVEL FRAGMENTATION OF 3-LITHIO-3,6-DIHYDRO-1,2-OXAZINES - SYNTHESIS OF 2,5-DIHYDRO-2-FURANYLAMINES

被引:12
作者
DESAI, MC
DOTY, JL
STEPHENS, LM
BRIGHTY, KE
机构
[1] Central Research Division, Pfizer Inc, Groton
关键词
D O I
10.1016/S0040-4039(00)77465-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Cbz or N-Boc protected 3,6-dihydro-1,2-oxazines 1 on treatment with LDA at -78-degrees-C undergo a novel rearrangement to provide synthetically useful N-Cbz or N-Boc protected dihydro-2-furanylamines 2.
引用
收藏
页码:961 / 962
页数:2
相关论文
共 16 条
[1]   TOTAL SYNTHESIS OF (-)-NUPHARAMINE AND (+)-3-EPINUPHARAMINE VIA ASYMMETRIC NITROSO DIELS-ALDER REACTION [J].
AOYAGI, S ;
SHISHIDO, Y ;
KIBAYASHI, C .
TETRAHEDRON LETTERS, 1991, 32 (34) :4325-4328
[2]  
BALDWIN JE, 1984, TETRAHEDRON, V19, P3695
[3]   ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS FROM DIPOLE-STABILIZED CARBANIONS - THE TERT-BOC GROUP AS AN ACTIVATOR FOR ALPHA'-LITHIATION OF CARBAMATES [J].
BEAK, P ;
LEE, WK .
TETRAHEDRON LETTERS, 1989, 30 (10) :1197-1200
[4]   METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].
BEAK, P ;
ZAJDEL, WJ ;
REITZ, DB .
CHEMICAL REVIEWS, 1984, 84 (05) :471-523
[6]  
BOGER DL, 1987, HETERO DIELS ALDER M, pCH3
[7]   REACTIONS OF TRANSIENT-C-NITROSOCARBONYL COMPOUNDS WITH DIENES, MONOOLEFINS, AND NUCLEOPHILES [J].
CORRIE, JET ;
KIRBY, GW ;
MACKINNON, JWM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (04) :883-886
[8]  
DUEHOLM KL, 1992, SYNTHESIS-STUTTGART, P1
[9]   A NEW SYNTHETIC ROUTE TO TROPANE ALKALOIDS - PSEUDOTROPINE AND TROPACOCAINE [J].
IIDA, H ;
WATANABE, Y ;
KIBAYASHI, C .
TETRAHEDRON LETTERS, 1984, 25 (44) :5091-5094
[10]   MILD AND EFFICIENT METHODS FOR THE REDUCTIVE CLEAVAGE OF NITROGEN-OXYGEN BONDS [J].
KECK, GE ;
FLEMING, S ;
NICKELL, D ;
WEIDER, P .
SYNTHETIC COMMUNICATIONS, 1979, 9 (04) :281-286