Regio- and stereoselective microwave-assisted synthesis of 5-alkyl-4-alkenyl-4-phenyl-1,3-oxazolidin-2-ones

被引：4

作者：

Amador, Marta ^{[1
,2
]}

Ariza, Xavier ^{[1
,2
]}

Boyer, Jeremie ^{[1
,2
]}

D'Andrea, Lucia ^{[2
,3
]}

Garcia, Jordi ^{[1
,2
]}

Granell, Jaume ^{[2
,3
]}

机构：

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

[2] Univ Barcelona, IBUB, E-08028 Barcelona, Spain

[3] Univ Barcelona, Dept Quim Inorgan, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 06期

关键词：

Palladium catalysts; Nickel catalysts; Microwave-assisted synthesis; 1,4-Diols; Quaternary alpha-amino acids; CATALYZED ALLYLIC AMINATION; RAY MOLECULAR-STRUCTURE; ALPHA-AMINO-ACIDS; (-)-PHASEOLINIC ACID; MUSCLIDE-B; NICKEL; COMPLEX; ALK-2-YNE-1,4-DIOLS; ACETATE; (-)-METHYLENOLACTOCIN;

D O I：

10.1016/j.tetlet.2009.12.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral symmetrical alk-2-yne-1,4-diols have been stereoselectively transformed into 5-alkyl-4-alkenyl-4-phenyl-1,3-oxazolidin-2-ones, which are precursors of quaternary alpha-amino beta-hydroxy acids. The key step was the cyclization of the bis(tosylcarbamates) of 2-phenylalk-2-yne-1,4-diols, easily obtained from the starting chiral diols. These cyclizations were accomplished with complete regioselectivity and up to 92:8 dr in the presence of catalytic amounts of Ni(0) or Pd (II) derivatives under microwave heating. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：935 / 938

页数：4

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