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Type: Artigo de periódico
Title: Diastereoselective synthesis of 2,5-disubstituted tetrahydrofuran derivatives
Author: Pilli, RA
Riatto, VB
Abstract: 5-Substituted lactol 1 was converted to 2,5-disubstituted tetrahydrofuran derivatives by a Lewis acid-promoted reaction with allylsilanes. High trans selectivity (12:1) was obtained when hindered allylsilane 8 was employed. 5-Substituted lactol 16 was transformed into 2,5-cis-disubstituted tetrahydrofuran 17b (6:1 ratio) by a TiCl4-promoted intramolecular allyl transfer process. Additionally, 2,5-cis-disubstituted tetrahydrofuran derivatives were obtained in good yields and diastereoselectivities after alkyllithium addition to lactone 6, followed by Et3SiH/BF3. OEt2 reduction of the corresponding hemiketals. (C) 2000 Elsevier Science Ltd. All rights reserved.
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron-asymmetry. Pergamon-elsevier Science Ltd, v. 11, n. 18, n. 3675, n. 3686, 2000.
Rights: fechado
Identifier DOI: 10.1016/S0957-4166(00)00351-7
Date Issue: 2000
Appears in Collections:Unicamp - Artigos e Outros Documentos

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