Lewis acid catalyzed regioselective ring opening of azetidines with alcohols and thiols

An efficient synthesis of amino ethers and amino thioethers were achieved via the ring cleavage of N-tosylazetidines with alcohols or thiols. The reactions were studied in the presence of various Lewis acids and BF 3·OEt 2 was found to be the most efficient. The products were obtained in modest to g...

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 31; pp. 5375 - 5377
Main Authors Dwivedi, Sandeep K., Gandhi, Shikha, Rastogi, Namrata, Singh, Vinod K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.07.2007
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NONACTIVATED AZIRIDINES
CHLOROFORMATES
HYDROXYL COMPOUNDS
CLEAVAGE
LITHIUM
AROMATIC-AMINES
EFFICIENT METHOD
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Summary:An efficient synthesis of amino ethers and amino thioethers were achieved via the ring cleavage of N-tosylazetidines with alcohols or thiols. The reactions were studied in the presence of various Lewis acids and BF 3·OEt 2 was found to be the most efficient. The products were obtained in modest to good yields under very mild conditions in 5–15 min. An efficient synthesis of amino ethers and amino thioethers has been achieved via the ring cleavage of N-tosylazetidines with alcohols or thiols. The reactions were studied in the presence of various Lewis acids and BF 3·OEt 2 was found to be the most efficient. The products were obtained in modest to good yields under very mild conditions in 5–15 min.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.06.033