IODOCYCLIZATION OF ALLYLIC ALCOHOL DERIVATIVES CONTAINING INTERNAL NUCLEOPHILES - CONTROL OF STEREOSELECTIVITY BY SUBSTITUENTS IN THE ACYCLIC PRECURSORS

被引:159
作者
CHAMBERLIN, AR
DEZUBE, M
DUSSAULT, P
MCMILLS, MC
机构
关键词
D O I
10.1021/ja00356a020
中图分类号
O6 [化学];
学科分类号
0703 ;
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页码:5819 / 5825
页数:7
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共 26 条
[1]   PARTICIPATION OF A NEIGHBORING CARBOXYL GROUP IN ADDITION REACTIONS .1. THE MECHANISM OF THE REACTION OF BROMINE WITH GAMMA,DELTA-UNSATURATED ACIDS AND ESTERS [J].
ARNOLD, RT ;
CAMPOS, MD ;
LINDSAY, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (05) :1044-1047
[2]   HIGHLY STEREOSELECTIVE SYNTHESIS OF (+/-)-ALPHA-MULTISTRIATIN [J].
BARTLETT, PA ;
MYERSON, J .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1625-1627
[3]   STEREOSELECTIVE EPOXIDATION OF ACYCLIC OLEFINIC CARBOXYLIC-ACIDS VIA IODO-LACTONIZATION [J].
BARTLETT, PA ;
MYERSON, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (12) :3950-3952
[4]  
Bougault M. J., 1904, CR HEBD ACAD SCI, V139, P864
[5]   IODOLACTONIZATIONS USING THALLIUM(I) CARBOXYLATES [J].
CAMBIE, RC ;
HAYWARD, RC ;
ROBERTS, JL ;
RUTLEDGE, PS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (15) :1864-1867
[6]   ORIGIN OF PI-FACIAL STEREOSELECTIVITY IN ADDITIONS TO PI-BONDS - GENERALITY OF THE ANTI-PERIPLANAR EFFECT [J].
CARAMELLA, P ;
RONDAN, NG ;
PADDONROW, MN ;
HOUK, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2438-2440
[7]   STEREOSELECTIVE IODOLACTONIZATION OF ACYCLIC UNSATURATED 3-HYDROXYACIDS [J].
CHAMBERLIN, AR ;
DEZUBE, M ;
DUSSAULT, P .
TETRAHEDRON LETTERS, 1981, 22 (46) :4611-4614
[8]   SYNTHESIS OF THE POLYETHER ANTIBIOTIC MONENSIN .2. PREPARATION OF INTERMEDIATES [J].
COLLUM, DB ;
MCDONALD, JH ;
STILL, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :2118-2120
[9]  
COREY EJ, 1979, TETRAHEDRON LETT, V32, P335
[10]   KINETICS AND MECHANISM OF IODOLACTONIZATION OF GAMMA DELTA-UNSATURATED ACIDS [J].
DOAMARAL, L ;
MELO, SC .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (04) :800-802