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|Type:||Artigo de periódico|
|Title:||Diastereoselective synthesis of 2,5-disubstituted tetrahydrofuran derivatives|
|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.|
|Editor:||Pergamon-elsevier Science Ltd|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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