Allylations of chelated enolates using dienyl substrates

被引:9
作者
Basak, Sankar [1 ]
Kazmaier, Uli [1 ]
机构
[1] Univ Saarland, Inst Organ Chem, D-66123 Saarbrucken, Germany
关键词
D O I
10.1021/ol702865q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isomerization-free reactions of dienyl carbonates (1-3) with chelated amino acid ester enolates at -78 degrees C provide important information concerning the mechanism of these dienylations. The formation of regioisomeric products can be explained by competing S(N)2/S(N)2' reactions, and the product distribution can be influenced by proper choice of the reaction conditions.
引用
收藏
页码:501 / 504
页数:4
相关论文
共 69 条
[1]  
Acemoglu L., 2002, HDB ORGANOPALLADIUM, V2, P1689, DOI DOI 10.1002/0471212466.CH71
[2]   Use of tricyclohexylphosphine to control regiochemistry in palladium-catalyzed allylic alkylation [J].
Blacker, AJ ;
Clarke, ML ;
Loft, MS ;
Williams, JMJ .
ORGANIC LETTERS, 1999, 1 (12) :1969-1971
[3]   First-principles investigation of enantioselective catalysis: Asymmetric allylic amination with Pd complexes bearing P,N-ligands [J].
Blochl, PE ;
Togni, A .
ORGANOMETALLICS, 1996, 15 (20) :4125-4132
[4]   MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].
BROWN, JM ;
HULMES, DI ;
GUIRY, PJ .
TETRAHEDRON, 1994, 50 (15) :4493-4506
[5]   ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES [J].
CONSIGLIO, G ;
WAYMOUTH, RM .
CHEMICAL REVIEWS, 1989, 89 (01) :257-276
[6]  
Deska J, 2007, ANGEW CHEM, V119, p[4570, 4654]
[7]   Highly stereoselective peptide modifications through Pd-catalyzed allylic alkylations of chelated peptide enolates [J].
Deska, Jan ;
Kazmaier, Uli .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (21) :6204-6211
[8]  
Fagnou K, 2002, ANGEW CHEM INT EDIT, V41, P26, DOI 10.1002/1521-3773(20020104)41:1<26::AID-ANIE26>3.0.CO
[9]  
2-9
[10]  
Fairlamb IJS, 2002, CHEM-EUR J, V8, P4443, DOI 10.1002/1521-3765(20021004)8:19<4443::AID-CHEM4443>3.0.CO