An efficient synthesis of (pyrrolidin-2-ylidene)glycinate using intramolecular 1, 3-dipolar cycloaddition of azide and olefin

Methyl and tert-butyl ( E-)-(pyrrolidin-2-ylidene)glycinates 3a and 3b were efficiently and stereoselectively synthesized from 2, 3, 5-tri- O-benzylarabinose using Horner-Emmons olefination of arabinal 9 and phosphorylglycine ester and intramolecular 1, 3-dipolar cycloaddition reaction of azide and...

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Published inTetrahedron Vol. 55; no. 44; pp. 12723 - 12740
Main Authors Konda, Yaeko, Sato, Takahiro, Tsushima, Kaori, Dodo, Masataka, Kusunoki, Ami, Sakayanagi, Masataka, Sato, Noriko, Takeda, Kazuyoshi, Harigaya, Yoshihiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.10.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AZINOMYCIN-A
ANTITUMOR ANTIBIOTICS
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Summary:Methyl and tert-butyl ( E-)-(pyrrolidin-2-ylidene)glycinates 3a and 3b were efficiently and stereoselectively synthesized from 2, 3, 5-tri- O-benzylarabinose using Horner-Emmons olefination of arabinal 9 and phosphorylglycine ester and intramolecular 1, 3-dipolar cycloaddition reaction of azide and olefin as the key reactions. ( E)-(Pyrrolidin-2-ylidene)glycinates 3a and 3b were efficiently and stereoselectively synthesized from arabinose derivative by a Horner-Emmons olefination and a intramolecular 1, 3-dipolar cycloaddition reaction of azide and olefin as key reactions.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00753-X