Synthesis of amino acid derivatives via enantio- and diastereoselective Pd-catalyzed allylic substitutions with a non-stabilized enolate as nucleophile

被引：63

作者：

Weiss, TD

Helmchen, G

Kazmaier, U

机构：

[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany

[2] Univ Saarland, Inst Organ Chem, D-66123 Saarbrucken, Germany

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 12期

关键词：

D O I：

10.1039/b203791m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diastereomer ratios of up to 95:5 and enantiomeric excesses of up to 95% were achieved in Pd-catalyzed asymmetric allylic substitutions with zinc enolates of glycine esters as nucleophiles; a remarkable effect of the ligand on the diastereoselectivity of the substitution was found.

引用

页码：1270 / 1271

页数：2

共 21 条

[1]

Braun M, 2000, ANGEW CHEM INT EDIT, V39, P3494, DOI 10.1002/1521-3773(20001002)39:19<3494::AID-ANIE3494>3.0.CO

[2]

2-4

[3]

Braun M., 2000, ANGEW CHEM, V112, P3637

[4] Rapid microwave-induced palladium-catalyzed asymmetric allylic alkylation [J].

Bremberg, U ;

Larhed, M ;

Moberg, C ;

Hallberg, A .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1082-1083

[5] ISOLATION AND BIOSYNTHESIS OF CYCLOPENTENYLGLYCINE, A NOVEL NON-PROTEINOGENIC AMINO-ACID IN FLACOURTIACEAE [J].

CRAMER, U ;

REHFELDT, AG ;

SPENER, F .

BIOCHEMISTRY, 1980, 19 (13) :3074-3080

[6] Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis [J].

Helmchen, G ;

Pfaltz, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :336-345

[7] Enantioselective palladium-catalyzed allylic substitutions with asymmetric chiral ligands [J].

Helmchen, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :203-214

[8]

HELMCHEN G, 1999, 11 EUR S ORG CHEM ES, V11

[9]

Hoffmann H. M. R., 1995, ANGEW CHEM, V107, P73

[10] ISOLATION AND X-RAY CRYSTAL-STRUCTURE OF A PALLADACYCLOBUTANE - INSIGHT INTO THE MECHANISM OF CYCLOPROPANATION [J].

HOFFMANN, HMR ;

OTTE, AR ;

WILDE, A ;

MENZER, S ;

WILLIAMS, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (01) :100-102

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