REGIOCONTROLLED OPENING OF CYCLIC ETHERS USING DIMETHYLBORON BROMIDE

被引:118
作者
GUINDON, Y [1 ]
THERIEN, M [1 ]
GIRARD, Y [1 ]
YOAKIM, C [1 ]
机构
[1] MERCK FROSST CANADA INC,POINTE CLAIRE DOR H9R 4P8,QUEBEC,CANADA
关键词
D O I
10.1021/jo00385a007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:1680 / 1686
页数:7
相关论文
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[1]   NEW METHODS OF FORMATION OF META-SUBSTITUTED AROMATIC-COMPOUNDS [J].
ADAMS, J ;
BELLEY, M .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) :3878-3881
[2]   NUCLEOPHILIC CATALYSIS IN THE INSERTION OF SILICON HALIDES INTO OXIRANES - A SYNTHESIS OF ORTHO-PROTECTED VICINAL HALOHYDRINS [J].
ANDREWS, GC ;
CRAWFORD, TC ;
CONTILLO, LG .
TETRAHEDRON LETTERS, 1981, 22 (39) :3803-3806
[3]   BASE STRENGTHS OF SOME SATURATED CYCLIC ETHERS IN AQUEOUS SULFURIC ACID [J].
ARNETT, EM ;
WU, CY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (09) :1684-&
[4]   CONVERSION OF EPOXIDES TO BROMOHYDRINS BY B-BROMOBIS (DIMETHYLAMINO) BORANE [J].
BELL, TW ;
CIACCIO, JA .
TETRAHEDRON LETTERS, 1986, 27 (07) :827-830
[5]   A GENERAL-METHOD FOR DETERMINING THE ANOMERIC CONFIGURATION OF C-FURANOSIDE DERIVATIVES - A H-1 NUCLEAR-MAGNETIC-RESONANCE NUCLEAR OVERHAUSER EFFECT STUDY [J].
BERNSTEIN, MA ;
MORTON, HE ;
GUINDON, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (08) :1155-1163
[6]   PLATINUM-CATALYZED ACYLATIVE CLEAVAGE OF CYCLIC ETHERS [J].
FITCH, JW ;
PAYNE, WG ;
WESTMORELAND, D .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (05) :751-753
[7]   CLEAVAGE OF CYCLIC ETHERS BY MAGNESIUM BROMIDE ACETIC ANHYDRIDE - SN2 SUBSTITUTION AT A SECONDARY SITE [J].
GOLDSMITH, DJ ;
KENNEDY, E ;
CAMPBELL, RG .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (24) :3571-3574
[8]   DIMETHYLBORON BROMIDE AND DIPHENYLBORON BROMIDE - CLEAVAGE OF ACETALS AND KETALS [J].
GUINDON, Y ;
YOAKIM, C ;
MORTON, HE .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :3912-3920
[9]   DEOXYGENATION OF SULFOXIDES WITH BORON BROMIDE REAGENTS [J].
GUINDON, Y ;
ATKINSON, JG ;
MORTON, HE .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4538-4540
[10]   PREPARATION OF ETHYL 5(S),6-EPOXY-3(R)-(METHOXYMETHOXY)HEXANOATE - A KEY CHIRAL INTERMEDIATE FOR MEVINOLIN AND COMPACTIN [J].
GUINDON, Y ;
YOAKIM, C ;
BERNSTEIN, MA ;
MORTON, HE .
TETRAHEDRON LETTERS, 1985, 26 (09) :1185-1188