Synthesis of bis-α-amino acids through proline catalyzed asymmetric α-amination of higher homologs of Garner's aldehyde

被引：12

作者：

Petakamsetty, Ramu ^{[1
]}

Das, Ram Pada ^{[1
]}

Ramapanicker, Ramesh ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON | 2014年 / 70卷 / 50期

关键词：

Unusual amino acids; Organocatalysis; Asymmetric amination; Proline catalyzed reaction; STEREOSELECTIVE-SYNTHESIS; MESO-2,6-DIAMINOPIMELIC ACID; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; (S,S)-2,7-DIAMINOSUBERIC ACID; DAP; EFFICIENT; DIMERIZATION; DERIVATIVES; GLYCINE; ANALOGS;

D O I：

10.1016/j.tet.2014.10.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A very convenient synthesis of bis-alpha-amino acids from the higher homologs of Garner's aldehyde is reported. The key step is proline catalyzed asymmetric amination of the aldehydes using dibenzylazo-dicarboxylate. The aldehydes used are either commercially available or can easily be prepared from aspartic or glutamic acid. One of the two chiral centers in the bis-amino acids comes from the aldehyde and the other one is generated through the proline catalyzed reaction, which were high yielding and proceeded with very high diastereoselectivity (93-99%). The reported route offers a general method for the synthesis of the title compounds with desired stereochemical outcome. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：9554 / 9563

页数：10

共 41 条

[1] Asymmetric Synthesis of Sphinganine and Clavaminol H [J].

Ait-Youcef, Ramzi ;

Moreau, Xavier ;

Greck, Christine .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5312-5315

[2] Asymmetric α-Amination of Chiral Protected β-Hydroxyaldehydes Catalyzed by Proline [J].

Ait-Youcef, Ramzi ;

Sbargoud, Kamal ;

Moreau, Xavier ;

Greck, Christine .

SYNLETT, 2009, (18) :3007-3010

[3] Asymmetric oxidative dimerization of the enolates of N-[bis(methylthio)methylene]- and N-(diphenylmethylene)glycine esters [J].

AlvarezIbarra, C ;

Csaky, AG ;

Colmenero, B ;

Quiroga, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2478-2482

[4] Asymmetric synthesis of meso- and (2R,4R)-2,4-diaminoglutaric acids [J].

Avenoza, A ;

Cativiela, C ;

Peregrina, JM ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :863-871

[5]

Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO

[6]

2-Y

[7]

Brase S., 2012, COMPR CHIRALITY, V6, P374

[8] Enantiomerically pure α-amino acid synthesis via hydroboration -: Suzuki cross-coupling [J].

Collier, PN ;

Campbell, AD ;

Patel, I ;

Raynham, TM ;

Taylor, RJK .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1802-1815

[9] A concise, stereoselective synthesis of meso-2,6-diaminopimelic acid (DAP) [J].

Collier, PN ;

Patel, I ;

Taylor, RJK .

TETRAHEDRON LETTERS, 2001, 42 (34) :5953-5954

[10] Bacterial diaminopimelate metabolism as a target for antibiotic design [J].

Cox, RJ ;

Sutherland, A ;

Vederas, JC .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (05) :843-871

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