Study on the regioselectivity of the reaction of alpha-unsaturated organozinc compounds with alpha-imino esters from 2-amino or 3-amino alcohols .3. Synthesis of 3-amino-1,5 (or 1,6)-diols, cyclization into substituted 3-prop-1-enylmorpholines and to 5-s-butyl-2,3-dihydro-6H-1,4-coxazines

被引:1
作者
Courtois, G [1 ]
Miginiac, L [1 ]
机构
[1] UNIV POITIERS,SYNTH ORGAN LAB,CNRS,URA 574,F-86022 POITIERS,FRANCE
关键词
organic synthesis; aminodiols; allylic aminoesters; cyclization; morpholines; 2,3-dihydro-1,4-oxazines;
D O I
10.1016/0022-328X(95)06053-Y
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
O-silylated alpha-aminoesters, resulting from the regioselective reaction between organozinc derivatives and alpha-iminoesters hearing an alcohol group, are transformed into 3-amino-1,5 (or 1,6)-diols; then 2-allylic-3-amino-1,5-diols are converted into 3-prop-1-enylmorpholines or into 5-s-butyl-2,3-dihydro-6H-1,4-oxazines.
引用
收藏
页码:37 / 45
页数:9
相关论文
共 20 条
[1]  
*ACTA, 1993, IND PHYT, P126
[2]  
AUBELCHAZOT C, 1994, THESIS U LYON 1
[3]   TRIPHENYLPHOSPHINE-TETRACHLOROMETHANE PROMOTED CHLORINATION AND CYCLODEHYDRATION OF SIMPLE DIOLS [J].
BARRY, CN ;
EVANS, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) :3361-3364
[4]  
BUCHEL KH, 1982, CHEM PESTICIDES, P306
[5]   STEREOCONTROLLED ONE-POT CONVERSIONS OF ALPHA-ALKOXY ESTERS TO SYN-1,2-DIOL AND ANTI-1,2-DIOL DERIVATIVES [J].
BURKE, SD ;
DEATON, DN ;
OLSEN, RJ ;
ARMISTEAD, DM ;
BLOUGH, BE .
TETRAHEDRON LETTERS, 1987, 28 (34) :3905-3906
[6]   A ONE-STEP CONVERSION OF ESTERS TO SECONDARY ALCOHOLS WITH LIBH4-RMGX [J].
COMINS, DL ;
HERRICK, JJ .
TETRAHEDRON LETTERS, 1984, 25 (13) :1321-1324
[7]   REGIOSELECTIVITY OF THE REACTION OF ORGANOZINC COMPOUNDS WITH ALPHA-IMINOESTERS DERIVED FROM 2-AMINO OR 3-AMINO ALCOHOLS .2. SYNTHESIS OF 3-SUBSTITUTED HEXAHYDRO-1,4-OXAZEPIN-2-ONES AND TETRAHYDRO-1,4-OXAZIN-2-ONES [J].
COURTOIS, G ;
MIGINIAC, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 452 (1-2) :5-12
[8]   REGIOSELECTIVITY OF THE REACTION OF ORGANOZINC COMPOUNDS WITH ALPHA-IMINO ESTERS FROM 2-AMINO AND 3-AMINO ALCOHOLS .1. SYNTHESIS OF POLYFUNCTIONAL ALPHA-AMINO ESTERS [J].
COURTOIS, G ;
MIGINIAC, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 450 (1-2) :33-40
[9]  
GAYLORD NG, 1956, REDUCTION COMPLEX ME, P391
[10]  
Gillis BernardT., 1963, J. Org. Chem, V28, P1388