Stereoselective synthesis of substituted 5-hydroxy-1, 3-dioxanes

DC Forbes, DG Ene, MP Doyle

Index: Forbes, David C.; Ene, Doina G.; Doyle, Michael P. Synthesis, 1998 , # 6 p. 879 - 882

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Citation Number: 30

Abstract

Abstract: A series of 5-hydroxy-1, 3-dioxanes has been synthesized using a practical three- step strategy beginning with acetal/ketal formation of tris (hydroxymethyl) aminomethane followed by oxidative cleavage of the amino alcohol. After the ketone was revealed, stereoselective reduction with common hydride reagents, LiAlH4 for the trans isomers and L- Selectride for the cis analogues, gave the target compounds in high yield. Key words: 5- ...