Enantioselective synthesis of N,O-psiconucleosides

被引：35

作者：

Chiacchio, U

Borrello, L

Iannazzo, D

Merino, P

Piperno, A

Rescifina, A

Richichi, B

Romeo, G

机构：

[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy

[2] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy

[3] Univ Zaragoza, Fac Ciencias, Dept Quim Organ, ICMA, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 16期

关键词：

D O I：

10.1016/S0957-4166(03)00525-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first enantioselective synthesis Of beta-D and beta-L N,O-psiconucleosides is reported. The synthetic approach is based on the asymmetric 1.3-dipolar cycloaddition of the C-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methyl nitrone with ethyl 2-acetyl-oxyacrylate followed by Vorbruggen nucleosidation, and removal of the chiral auxiliary. Stereochemical assignments are supported by a DFT theoretical study of the cycloaddition reaction. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：2419 / 2425

页数：7

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