Efficient 1,5-chirality transfer in palladium-catalyzed allylic alkylations of chelated amino acid ester enolates

被引：54

作者：

Kazmaier, U ^{[1
]}

Lindner, T ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 21期

关键词：

allylation; amino acids; chelates; enolates; palladium;

D O I：

10.1002/anie.200500095

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Neither the olefin geometry nor the configuration of secondary allylic substrates in palladium-catalyzed allylic alkylations of chelated enolates has an influence on the newly formed stereogenic center of the amino acid (see scheme, TBDPS = tert- butyldiphenylsilyl, Tfa = trifluoroacetyl). This is controlled exclusively by the protecting group on the chiral center. Therefore, the choice of the protecting group on the allylic alcohol can lead to either of the diastereomeric amino acids in a highly stereoselective fashion. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：3303 / 3306

页数：4

相关论文

共 50 条

[1] 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

[2] 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

[3] 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

[4] 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

[5]

CORRADIN.P, 1966, CHEM COMMUN, P618

[6] 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

[7] 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

[8] 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

[9] SYNTHESIS OF ALPHA-AMINO-ACIDS BY CATALYTIC PALLADIUM (O) ALKYLATION OF SCHIFF-BASES [J].

FERROUD, D ;

GENET, JP ;

KIOLLE, R .

TETRAHEDRON LETTERS, 1986, 27 (01) :23-26

[10] Enantioselective allylic substitution catalyzed by an iridium complex: remarkable effects of the counter cation [J].

Fuji, K ;

Kinoshita, N ;

Tanaka, K ;

Kawabata, T .

CHEMICAL COMMUNICATIONS, 1999, (22) :2289-2290

← 1 2 3 4 5 →