Catalytic asymmetric addition of dialkylzinc reagents to α-aldiminoesters

被引：38

作者：

Basra, Sandeep ^{[1
]}

Fennie, Michael W. ^{[1
]}

Kozlowski, Marisa C. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 13期

关键词：

D O I：

10.1021/ol0602093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic, enantioselective addition of organozinc reagents to alpha-aldiminoesters is described. The use of a Lewis acid/Lewis base containing bifunctional catalyst preorganizes both reactive substrates to promote enantioselective addition over the racemic background reaction and alternative addition modes. Alcohol additives were found to enhance the enantioselection. The addition product was also found to cyclize with remaining substrate to provide imidazolidines.

引用

页码：2659 / 2662

页数：4

共 43 条

[1]

Bertrand MP, 1999, SYNLETT, P1148

[2]

BERTRAND MP, 2002, TETRAHEDRION, V56, P3951

[3] Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines.: A practical synthesis of α-chiral amines [J].

Boezio, AA ;

Charette, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1692-1693

[4] Diastereoselective addition of organozinc reagents to chiral α-imino esters [J].

Chiev, KP ;

Roland, S ;

Mangeney, P .

TETRAHEDRON-ASYMMETRY, 2002, 13 (20) :2205-2209

[5] Asymmetric synthesis of quaternary α- and β-amino acids and β-lactams via proline-catalyzed Mannich reactions with branched aldehyde donors [J].

Chowdari, NS ;

Suri, JT ;

Barbas, CF .

ORGANIC LETTERS, 2004, 6 (15) :2507-2510

[6] The direct catalytic asymmetric Mannich reaction [J].

Córdova, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) :102-112

[7] The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands [J].

Dahmen, S ;

Bräse, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5940-5941

[8] Development of bifunctional salen catalysts:: Rapid, chemoselective alkylations of α-ketoesters [J].

DiMauro, EF ;

Kozlowski, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12668-12669

[9] Synthesis, characterization, and metal complexes of a salen ligand containing a quinoline base [J].

DiMauro, EF ;

Mamai, A ;

Kozlowski, MC .

ORGANOMETALLICS, 2003, 22 (04) :850-855

[10] The first catalytic asymmetric addition of dialkylzincs to α-ketoesters [J].

DiMauro, EF ;

Kozlowski, MC .

ORGANIC LETTERS, 2002, 4 (22) :3781-3784

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