Practical and highly enantioselective synthesis of β-alkynyl-β-amino esters through Ag-catalyzed asymmetric Mannich reactions of silylketene acetals and alkynyl imines

被引：83

作者：

Josephsohn, NS ^{[1
]}

Carswell, EL ^{[1
]}

Snapper, ML ^{[1
]}

Hoveyda, AH ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol050910r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A readily available iso-leucine-based phosphine ligand is used to promote Ag-catalyzed Mannich reactions between silylketene acetals and various alkynyl imines. Reactions can be effected in the presence of 5 mol % catalyst, without the need for rigorous exclusion of air, and with commercially available solvents (without purification) to afford the desired beta-alkynyl-beta-amino esters in 84-94% ee and 61-91% isolated yield.

引用

页码：2711 / 2713

页数：3

共 43 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[2] Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines [J].

Akullian, LC ;

Snapper, ML ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4244-4247

[3] Asymmetric synthesis of 2-alkyl- and 2-aryl-3-aminopropionic acids (β2-amino acids) from (S)-N-acryloyl-5,5-dimethyloxazolidin-2-one SuperQuat derivatives [J].

Beddow, JE ;

Davies, SG ;

Smith, AD ;

Russell, AJ .

CHEMICAL COMMUNICATIONS, 2004, (23) :2778-2779

[4] Catalytic asymmetric Mannich reactions of glycine derivatives with imines.: A new approach to optically active α,β-diamino acid derivatives [J].

Bernardi, L ;

Gothelf, AS ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2583-2591

[5] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].

Cardillo, G ;

Tomasini, C .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&

[6] The direct catalytic asymmetric cross-Mannich reaction:: A highly enantioselective route to 3-amino alcohols and α-amino acid derivatives [J].

Córdova, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (08) :1987-1997

[7] A very short, efficient and inexpensive synthesis of the prodrug form of SC-54701A - A platelet aggregation inhibitor [J].

Cossy, J ;

Schmitt, A ;

Cinquin, C ;

Buisson, D ;

Belotti, D .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (13) :1699-1700

[8]

COZZI PG, 2005, ANGEW CHEM, V44, pASAP

[9] Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts [J].

Ferraris, D ;

Young, B ;

Dudding, T ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4548-4549

[10] Mechanism of palladium complex-catalyzed enantioselective Mannich-type reaction: Characterization of a novel binuclear palladium enolate complex [J].

Fujii, A ;

Hagiwara, E ;

Sodeoka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5450-5458

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