Regioselective palladium-catalyzed allylic alkylations via anti/syn-π-allyl intermediates

被引：50

作者：

Kazmaier, U ^{[1
]}

Pohlman, M ^{[1
]}

机构：

[1] Univ Saarland, Dept Organ Chem, D-66041 Saarbrucken, Germany

来源：

SYNLETT | 2004年 / 04期

关键词：

allylic alkylation; amino acids; chelated enolates; palladium; pi-sigma-pi-isomerization;

D O I：

10.1055/s-2004-817776

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly reactive chelated enolates are versatile nucleophiles for palladium-catalyzed allylic alkylations, which react already at -78 degreesC. Therefore, typical side reactions such pi-sigma-pi-isomerizations can be suppressed. Suitably substituted (Z)-allylic substrates give rise to anti/syn-pi-allyl complexes, which react regioselectively with these nucleophiles at the anti-position.

引用

页码：623 / 626

页数：4

共 39 条

[1]

Acemoglu L, 2001, ADV SYNTH CATAL, V343, P75, DOI 10.1002/1615-4169(20010129)343:1<75::AID-ADSC75>3.0.CO

[2]

2-W

[3] ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES [J].

CONSIGLIO, G ;

WAYMOUTH, RM .

CHEMICAL REVIEWS, 1989, 89 (01) :257-276

[4]

CORRADINI P, 1966, J CHEM SOC CHEM COMM, P618

[5]

Fairlamb IJS, 2002, CHEM-EUR J, V8, P4443, DOI 10.1002/1521-3765(20021004)8:19<4443::AID-CHEM4443>3.0.CO

[6]

2-3

[7] Highly selective palladium catalyzed kinetic resolution and enantioselective substitution of racemic allylic carbonates with sulfur nucleophiles: Asymmetric synthesis of allylic sulfides, allylic sulfones, and allylic alcohols [J].

Gais, HJ ;

Jagusch, T ;

Spalthoff, N ;

Gerhards, F ;

Frank, M ;

Raabe, G .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (17) :4202-4221

[8]

Godleslcy S., 1991, COMPREHENSIVE ORGANI, V4, P585

[9] Retention of regiochemistry of allylic esters in palladium-catalyzed allylic alkylation in the presence of a MOP ligand [J].

Hayashi, T ;

Kawatsura, M ;

Uozumi, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1681-1687

[10]

HEGEDUS LS, 1999, T METALS SYNTHESIS C

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