New developments in stereoselective palladium-catalyzed allylic alkylations of preformed enolates

被引：55

作者：

Braun, M ^{[1
]}

Meier, T ^{[1
]}

机构：

[1] Univ Dusseldorf, Inst Organ Chem & Makromol Chem, D-40225 Dusseldorf, Germany

来源：

SYNLETT | 2006年 / 05期

关键词：

chirality; catalysis; substitution; carbon-carbon bond formation; asymmetric synthesis;

D O I：

10.1055/s-2006-933138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Whereas the enantioselective palladium-catalyzed allylic substitution with 'soft', stabilized carbanions can be considered as established and versatile method today, nonstabilized, preformed enolates were used for this purpose only very reluctantly. This report focuses on progress made recently in combining pi-allyl palladium complexes with different metal enolates derived from carboxylic esters and ketones. The elaboration of protocols that permit enantioselective and - at the same time - diastereoselective allylic alkylations are emphasized in this report. The stereochemistry in the approach of the enolate to the pi-allyl palladium complex is also discussed.

引用

页码：661 / 676

页数：16

共 111 条

[1] SUCCESSFUL APPLICATION OF A FORGOTTEN PHOSPHINE IN ASYMMETRIC CATALYSIS - A 9-PHOSPHABICYCLO[3.3.1]NON-9-YL FERROCENE DERIVATIVE AS CHIRAL LIGAND [J].

ABBENHUIS, HCL ;

BURCKHARDT, U ;

GRAMLICH, V ;

KOLLNER, C ;

PREGOSIN, PS ;

SALZMANN, R ;

TOGNI, A .

ORGANOMETALLICS, 1995, 14 (02) :759-766

[2] Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation [J].

Alexakis, A ;

Polet, D .

ORGANIC LETTERS, 2004, 6 (20) :3529-3532

[3]

[Anonymous], COMPREHENSIVE ORGANO

[4]

[Anonymous], ANGEW CHEM

[5]

[Anonymous], ANGEW CHEM

[6]

ATKINS KE, 1970, TETRAHEDRON LETT, P3821

[7]

Bartels B, 2003, EUR J ORG CHEM, V2003, P1097

[8] The enantioselective Tsuji allylation [J].

Behenna, DC ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045

[9] Molybdenum-catalyzed asymmetric allylic alkylations [J].

Belda, O ;

Moberg, C .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (03) :159-167

[10] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

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