Stereoselective methoxyselenenylation of acyclic allylic alcohol derivatives: A method for the synthesis of 1,3-anti-diols

被引:15
作者
Kim, KS [1 ]
Park, HB [1 ]
Kim, JY [1 ]
Ahn, YH [1 ]
Jeong, IH [1 ]
机构
[1] YONSEI UNIV,DEPT CHEM,WONJU 220710,SOUTH KOREA
关键词
D O I
10.1016/0040-4039(95)02408-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of secondary acyclic trans-allylic alcohol derivatives with PhSeBr in the presence of 2,6-di-t-butylpyridine in MeOH proceeded in a highly regio- and stereoselective manner and the subsequent reduction and deprotection of the resultant methoxyselenides afforded mostly 1,3-anti-diols. The methoxyselenenylation of the acetate derivative of the same allylic alcohol, on the other hand, gave several other isomers along with the 1,3-anti-diol derivative.
引用
收藏
页码:1249 / 1252
页数:4
相关论文
共 10 条
[1]   METHODOLOGY TO ESTABLISH 1,2-DIFUNCTIONALITY AND 1,3-DIFUNCTIONALITY FOR THE SYNTHESIS OF CARBOHYDRATE-DERIVATIVES [J].
AGER, DJ ;
EAST, MB .
TETRAHEDRON, 1992, 48 (14) :2803-2894
[2]  
[Anonymous], 1987, Organoselenium Chemistry
[3]   UNUSUAL ATTRACTIVE INTERACTIONS BETWEEN SELENIUM AND OXYGEN IN SELENOIMINOQUINONES [J].
BARTON, DHR ;
HALL, MB ;
LIN, ZY ;
PAREKH, SI ;
REIBENSPIES, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5056-5059
[4]   COMPUTATIONAL STUDIES OF NONBONDED SULFUR OXYGEN AND SELENIUM OXYGEN INTERACTIONS IN THE THIAZOLE AND SELENAZOLE NUCLEOSIDES [J].
BURLING, FT ;
GOLDSTEIN, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2313-2320
[5]   HYDROXYSELENATION OF ALLYLIC ALCOHOLS [J].
COOPER, MA ;
WARD, AD .
TETRAHEDRON LETTERS, 1995, 36 (13) :2327-2330
[6]   DETERMINING ABSOLUTE-CONFIGURATIONS OF STEREOCENTERS IN ANNONACEOUS ACETOGENINS THROUGH FORMALDEHYDE ACETAL DERIVATIVES AND MOSHER ESTER METHODOLOGY [J].
GU, ZM ;
ZENG, L ;
FANG, XP ;
COLMANSAIZARBITORIA, T ;
HUO, M ;
MCLAUGHLIN, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5162-5172
[7]   HYDROXYSELENATION OF ACETOXYCYCLOHEX-2-ENE [J].
HAUGHAN, AF ;
KNIGHT, JR ;
SWEENEY, JB .
TETRAHEDRON LETTERS, 1994, 35 (11) :1781-1784
[8]   ORIGINS OF REGIOSELECTIVITY AND STEREOSELECTIVITY IN ADDITIONS OF PHENYLSELENENYL CHLORIDE TO ALLYLIC ALCOHOLS AND THE APPLICABILITY OF THESE ADDITIONS TO A SIMPLE 1,3-ENONE TRANSPOSITION SEQUENCE [J].
LIOTTA, D ;
ZIMA, G ;
SAINDANE, M .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1258-1267
[9]  
Paulmier C., 1986, ORGANIC SYNTHESIS
[10]   ANALYSIS OF 2 C-13 NMR CORRELATIONS FOR DETERMINING THE STEREOCHEMISTRY OF 1,3-DIOL ACETONIDES [J].
RYCHNOVSKY, SD ;
ROGERS, B ;
YANG, G .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (13) :3511-3515