Substrate-controlled palladium-catalyzed allylic alkylations of chelated enolates - Scope and limitations

被引：25

作者：

Lindner, T ^{[1
]}

Kazmaier, U ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 11-13期

关键词：

allylic alkylation; amino acids; chelates; enolates; palladium; stereoselective synthesis;

D O I：

10.1002/adsc.200505140

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Chelated enolates of amino acid derivatives were found to be excellent nucleophiles for stereoselective palladium-catalyzed allylic alkylations via terminal pi-allyl complexes. Neither the olefin geometry (linear substrates) nor the configuration of secondary allylic substrates has an influence on the newly formed stereogenic centre of the amino acid. This is exclusively controlled by the protecting group on

引用

页码：1687 / 1695

页数：9

共 73 条

[1] Convenient preparations of (diphenylphosphono)acetic and esters and the comparison of the Z-selectivities of their Horner-Wadsworth-Emmons reaction with aldehydes depending on the ester moiety [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8406-8408

[2] Enantioselective catalysis using phosphorus-donor ligands containing two or three P-N or P-O bonds [J].

Ansell, J ;

Wills, M .

CHEMICAL SOCIETY REVIEWS, 2002, 31 (05) :259-268

[3] ALPHA-AMINO ESTER DERIVATIVES AS NUCLEOPHILES IN STEREOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS [J].

BALDWIN, IC ;

WILLIAMS, JMJ ;

BECKETT, RP .

TETRAHEDRON-ASYMMETRY, 1995, 6 (07) :1515-1518

[4] Ir-catalysed allylic substitution: mechanistic aspects and asymmetric synthesis with phosphorus amidites as ligands [J].

Bartels, B ;

Helmchen, G .

CHEMICAL COMMUNICATIONS, 1999, (08) :741-742

[5] Stereospecific and stereodivergent construction of quaternary carbon centers through switchable directed/nondirected allylic substitution [J].

Breit, B ;

Demel, P ;

Studte, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3786-3789

[6]

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

[7] STUDY ON THE REGIOSELECTIVITY OF CARBANION SUBSTITUTION BY MEANS OF ALLYLIC DERIVATIVES CATALYZED TO PALLADIUM - SELECTIVE ACQUISITION OF COMPOUNDS WITH QUARTERNARY CARBON-ATOMS [J].

CUVIGNY, T ;

JULIA, M ;

ROLANDO, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :395-413

[8] Conservation of absolute configuration in the acyclic rhodium-catalyzed allylic alkylation reaction:: Evidence for an enyl (σ+π) organorhodium intermediate [J].

Evans, PA ;

Nelson, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5581-5582

[9] Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: Diastereoselective approach to quaternary carbon stereogenic centers [J].

Evans, PA ;

Kennedy, LJ .

ORGANIC LETTERS, 2000, 2 (15) :2213-2215

[10] Regioselective rhodium-catalyzed allylic linchpin cross-coupling reactions:: Diastereospecific construction of anti-1,3-carbon stereogenic centers and C2-symmetrical fragments [J].

Evans, PA ;

Kennedy, LJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) :1234-1235

← 1 2 3 4 5 6 7 8 →