Stereoselective synthesis of carane-based chiral β- and γ-amino acid derivatives via conjugate addition

被引：7

作者：

Szakonyi, Zsolt ^{[1
]}

Csor, Arpad ^{[1
]}

Haukka, Matti ^{[2
]}

Fueloep, Ferenc ^{[1
,3
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, Eotvos Utca 6, H-6720 Szeged, Hungary

[2] Univ Jyvaskyla, Dept Chem, SF-40351 Jyvaskyla, Finland

[3] Hungarian Acad Sci, Stereochem Res Grp, H-6720 Szeged, Hungary

来源：

TETRAHEDRON | 2015年 / 71卷 / 29期

关键词：

beta-Amino acid; Carane; Chiral; Asymmetric synthesis; Michael addition; Rearrangement; HOMOCHIRAL ALPHA; BETA-UNSATURATED ESTERS; PURE LITHIUM AMIDES; ASYMMETRIC-SYNTHESIS; AMMONIA EQUIVALENTS; CHEMISTRY; (-)-ALPHA-PINENE; ANHYDRIDE; PEPTIDES; PRODUCTS; ALCOHOLS;

D O I：

10.1016/j.tet.2015.05.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael addition of dibenzylamine to (-)-tert-butyl isochaminate, prepared in three steps from (-)-perillaldehyde, furnished a carane-based beta-amino acid derivative in a highly stereospecific reaction. The resulting amino ester was transformed to the bicyclic amino acid, a promising building block for the synthesis of 1,3-heterocycles and peptidomimetics. The conjugate addition of nitromethane to alpha,beta-unsaturated methyl ester likewise resulted in nitro esters in stereospecific reactions. Catalytic reduction of the nitro group yielded a gamma-amino ester. Under acidic conditions, the hydrolysis of the methyl ester resulted in an unexpected aminolactone-type product through rearrangement of the bicyclic carane system, whereas an alternative synthetic pathway through alpha,beta-unsaturated benzyl ester furnished the desired gamma-amino acid. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：4846 / 4852

页数：7

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