Regioselectivity in the palladium-catalyzed addition of carbon nucleophiles to dihydropyran derivatives

被引:18
作者
Brescia, MR [1 ]
Shimshock, YC [1 ]
DeShong, P [1 ]
机构
[1] UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLLEGE PK,MD 20742
关键词
D O I
10.1021/jo961973d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselectivity of Pd-catalyzed malonate or sulfonylacetate addition to dihydropyran derivatives is highly dependent upon the substitution pattern of the dihydropyran nucleus and is governed by electronic, rather than steric factors. In certain instances, subtle steric features also play a role in controlling regioselectivity by altering the conformation of the intermediate eta(3)-allyl Pd-complex.
引用
收藏
页码:1257 / 1263
页数:7
相关论文
共 21 条
[1]   SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES [J].
ACHMATOWICZ, O ;
BUKOWSKI, P ;
SZECHNER, B ;
ZWIERZCHOWSKA, Z ;
ZAMOJSKI, A .
TETRAHEDRON, 1971, 27 (10) :1973-+
[2]  
ACHMATOWICZ O, 1973, ROCZ CHEM, V47, P99
[3]  
AKERMARK B, 1984, ORGANOMETALLICS, V3, P679
[4]   THE PREPARATION OF AMINO-SUGARS AND BRANCHED-CHAIN SUGARS BY PALLADIUM-CATALYZED, ALLYLIC SUBSTITUTION OF ALKYL HEX-2-ENOPYRANOSIDES [J].
BAER, HH ;
HANNA, ZS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (05) :889-906
[5]   REACTION OF 1,2-DIDEOXY-GLYC-1-ENOPYRANOSES AND 2-DEOXY-GLYCOPYRANOSES WITH HYDROGEN FLUORIDE .6. [J].
BOCK, K ;
PEDERSEN, C .
ACTA CHEMICA SCANDINAVICA, 1971, 25 (07) :2757-&
[6]  
CAREY FA, 1990, ADV ORGANIC CHEM A, P130
[7]   A FORMAL TOTAL SYNTHESIS OF (+/-)-PSEUDOMONIC ACID-A [J].
CLASS, YJ ;
DESHONG, P .
TETRAHEDRON LETTERS, 1995, 36 (42) :7631-7634
[8]   SELECTIVE MONO-CLAISEN REARRANGEMENT OF CARBOHYDRATE GLYCALS - A CHEMICAL CONSEQUENCE OF THE VINYLOGOUS ANOMERIC EFFECT [J].
CURRAN, DP ;
SUH, YG .
CARBOHYDRATE RESEARCH, 1987, 171 :161-191
[9]   PALLADIUM-CATALYZED COUPLING OF ALLYLIC ACETATES WITH ARYLSTANNANES AND VINYLSTANNANES [J].
DELVALLE, L ;
STILLE, JK ;
HEGEDUS, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3019-3023
[10]   PALLADIUM-ASSISTED C-GLYCOSYLATION - ADDITION OF CARBANIONS TO CYCLIC ENOL ETHERS [J].
DUNKERTON, LV ;
SERINO, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (14) :2812-2814