Regio- and enantioselective iridium-catalysed allylic aminations and alkylations of dienyl esters

被引：94

作者：

Lipowsky, G ^{[1
]}

Helmchen, G ^{[1
]}

机构：

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

来源：

CHEMICAL COMMUNICATIONS | 2004年 / 01期

关键词：

D O I：

10.1039/b311502j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Regio- and enantioselective iridium-catalysed allylic aminations and alkylations of dienyl substrates are presented; using phosphorus amidite L1 as ligand, aminations provided ee values of up to 97% and alkylations of up to 90%.

引用

页码：116 / 117

页数：2

共 21 条

[1] Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects [J].

Arnold, LA ;

Imbos, R ;

Mandoli, A ;

de Vries, AHM ;

Naasz, R ;

Feringa, BL .

TETRAHEDRON, 2000, 56 (18) :2865-2878

[2]

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

[3]

Bartels B, 2002, EUR J INORG CHEM, P2569

[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] Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents [J].

Feringa, BL ;

Pineschi, M ;

Arnold, LA ;

Imbos, R ;

de Vries, AHM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) :2620-2623

[6] 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

[7] First enantioselective alkylations of monosubstituted allylic acetates catalyzed by chiral iridium complexes [J].

Janssen, JP ;

Helmchen, G .

TETRAHEDRON LETTERS, 1997, 38 (46) :8025-8026

[8] Synthesis of β-substituted α-amino acids with use of iridium-catalyzed asymmetric allylic substitution [J].

Kanayama, T ;

Yoshida, K ;

Miyabe, H ;

Kimachi, T ;

Takemoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6197-6201

[9] Enantio- and diastereoselective Ir-catalyzed allylic substitutions for asymmetric synthesis of amino acid derivatives [J].

Kanayama, T ;

Yoshida, K ;

Miyabe, H ;

Takemoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (18) :2054-2056

[10] Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides [J].

López, F ;

Ohmura, T ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) :3426-3427

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