Enantioselective Organocatalytic Addition of Oxazolones to 1,1-Bis(phenylsulfonyl)ethylene: A Convenient Asymmetric Synthesis of Quaternary α-Amino Acids

被引：95

作者：

Alba, Andrea-Nekane R. ^{[1
]}

Companyo, Xavier ^{[1
]}

Valero, Guillem ^{[1
]}

Moyano, Albert ^{[1
]}

Rios, Ramon ^{[1
]}

机构：

[1] Univ Barcelona, Dept Organ Chem, Fac Chem, E-08028 Barcelona, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 18期

关键词：

amino acids; Michael addition; organocatalysis; oxazolones; stereoselectivity; PHASE-TRANSFER CATALYSTS; MICHAEL ADDITION; STEREOSELECTIVE-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; MEMORY; ALKYLATION; CHIRALITY; CONSTRUCTION; STEREOCENTERS; DERIVATIVES;

D O I：

10.1002/chem.200903025

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new, easy, and highly enantioselective method for the synthesis of quaternary alpha-alkyl-alpha-amino acids based on organocatalysis is reported. The addition of oxazolones to 1,1-bis(phenylsulfonyl)ethylene is efficiently catalyzed by simple chiral bases or thioureas. The reaction affords alpha,alpha-disubstituted alpha-amino acid derivatives with complete C4 regioselectivity and with excellent yields and enantioselectivities. This methodology is complementary to previously reported enantioselective approaches to quaternary alpha-amino acids and allows the synthesis of alpha-phenyl-alpha-alkyl-alpha-amino acids and alpha-tert-butyl-alpha-alkyl-alpha-amino acids. It has distinct advantages in terms of operational simplicity, enviromentally friendly conditions, and suitability for largescale reactions.

引用

页码：5354 / 5361

页数：8

共 80 条

[51] Aspartame dipeptide analogues: Effect of number of side-chain methylene group spacers and C-alpha-methylation in the second position [J].

Mossel, E ;

Formaggio, F ;

Crisma, M ;

Toniolo, C ;

Broxterman, QB ;

Boesten, WHJ ;

Kamphuis, J ;

Quaedflieg, PJLM ;

Temussi, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (08) :1305-1314

[52]

Nájera C, 2002, SYNLETT, P1388

[53] Catalytic asymmetric synthesis of α-amino acids [J].

Najera, Carmen ;

Sansano, Jose M. .

CHEMICAL REVIEWS, 2007, 107 (11) :4584-4671

[54] A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF ALPHA-METHYL AMINO-ACID DERIVATIVES BY PHASE-TRANSFER CATALYSIS [J].

ODONNELL, MJ ;

WU, SD .

TETRAHEDRON-ASYMMETRY, 1992, 3 (05) :591-594

[55] THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS BY PHASE-TRANSFER CATALYSIS [J].

ODONNELL, MJ ;

BENNETT, WD ;

WU, SD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) :2353-2355

[56] Enantio- and diastereoselective construction of α,α-disubstituted α-amino acids for the synthesis of biologically active compounds [J].

Ohfune, Y ;

Shinada, T .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (24) :5127-5143

[57] Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts [J].

Okino, T ;

Hoashi, Y ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12672-12673

[58] Practical catalytic enantioselective synthesis of α,α-dialkyl-α-amino acids by chiral phase-transfer catalysis [J].

Ooi, T ;

Takeuchi, M ;

Kameda, M ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) :5228-5229

[59]

Paglialunga Paradisi Mario, 1995, Tetrahedron, V51, P2379, DOI 10.1016/0040-4020(94)01095-H

[60] The chemistry of life's origin: A carbonaceous meteorite perspective [J].

Pizzarello, S .

ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (04) :231-237

← 1 2 3 4 5 6 7 8 →