The first enantioselective synthesis of β-D and β-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-acetyloxyacrylate followed by Vorbrüggen nucleosidation, and removal of the chiral auxiliary. Stereochemical assignments are supported by a DFT theoretical study of the cycloaddition reaction
Enantioselective synthesis of N,O-psiconucleoside / U. CHIACCHIO; B. LUISA; D. IANNAZZO; P. MERINO; A. PIPERNO; A. RESCIFINA; B. RICHICHI; G. ROMEO. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 14:(2003), pp. 2419-2425. [10.1016/S0957-4166(03)00525-1]
Enantioselective synthesis of N,O-psiconucleoside
RICHICHI, BARBARA;
2003
Abstract
The first enantioselective synthesis of β-D and β-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-acetyloxyacrylate followed by Vorbrüggen nucleosidation, and removal of the chiral auxiliary. Stereochemical assignments are supported by a DFT theoretical study of the cycloaddition reaction
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