Diastereoselective syntheses of 2-amino propargyl alcohols.: Chiral building blocks for enantiopure amino γ-lactones and 5-hydroxy-piperidinone derivatives

被引：21

作者：

Andres, Jose Maria ^{[1
]}

Pedrosa, Rafael ^{[1
]}

Perez-Encabo, Alfonso ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 30期

关键词：

alpha-amino aldehydes; asymmetric synthesis; diastereoselective addition; hydroxy-piperidinones; lactones; STEREOSELECTIVE-SYNTHESIS; AZA-ANNULATION; ROUTE; (+/-)-PROSOPININE; 2-AZETIDINONES; ALKALOIDS; ALDEHYDES; ADDITIONS; REAGENTS; ESTERS;

D O I：

10.1016/j.tetlet.2006.05.131

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Dibenzylamino aldehydes, derived from the corresponding natural alpha-amino acids, react with metal acetylides to yield anti-amino propargyl alcohols in good yield and diastereomeric excess. syn Amino alcohols are prepared from the. anti diastereo-isomers and all of them are elaborated in few steps to enantiopure amino lactones and hydroxy-piperidin-2-ones. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5317 / 5320

页数：4

共 24 条

[21] FROM AZIRIDINES TO CARBAPENEMS VIA A NOVEL BETA-LACTAM RING-CLOSURE - AN ENANTIOSELECTIVE SYNTHESIS OF (+)-PS-5 [J].

TANNER, D ;

SOMFAI, P .

TETRAHEDRON, 1988, 44 (02) :619-624

[22] ENANTIODIVERGENT AND DIASTEREODIVERGENT SYNTHESIS OF ALL 4 DIASTEREOMERS OF THE 2,6-DISUBSTITUTED 3-PIPERIDINOL CHIRAL BUILDING-BLOCK [J].

TOYOOKA, N ;

YOSHIDA, Y ;

MOMOSE, T .

TETRAHEDRON LETTERS, 1995, 36 (21) :3715-3718

[23] 2-piperidone type of chiral building block for 3-piperidinol alkaloid synthesis [J].

Toyooka, N ;

Yoshida, Y ;

Yotsui, Y ;

Momose, T .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4914-4919

[24] A NOVEL CHIRAL CYCLOPENTADIENYL LIGAND BASED ON EPHEDRINE [J].

VANDERZEIJDEN, AAH .

TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :913-918

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