Synlett 2012; 23(19): 2773-2776
DOI: 10.1055/s-0032-1317529
letter
© Georg Thieme Verlag Stuttgart · New York

A Mild, Room-Temperature Protection of Ketones and Aldehydes as 1,3-­Dioxolanes under Basic Conditions

Authors

  • Alfred Hassner*

    Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel   Fax: +972(3)7384053   Email: hassna@biu.ac.il
  • Chennakesava Reddy Bandi

    Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel   Fax: +972(3)7384053   Email: hassna@biu.ac.il
  • Sharad Panchgalle

    Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel   Fax: +972(3)7384053   Email: hassna@biu.ac.il
Further Information

Publication History

Received: 20 September 2012

Accepted after revision: 12 October 2012

Publication Date:
13 November 2012 (online)


Graphical Abstract

Preview

Abstract

Protection of ketones or aldehydes as 1,3-dioxolane derivatives proceeds within minutes at room temperature in the presence of N-hydroxybenzenesulfonamide, its O-benzyl derivative, or the tosyl analogue, in the absence of strong protonic acids, and in the presence of base (Et3N). Acid-sensitive groups such as O-THP, O-TBS, or N-Boc are unaffected.