1-Benzenesulfinyl Piperidine (BSP)/Triflic Anhydride: An Effective Combination for the Hydrolysis of Dithioacetals

Abstract

The combination of 1-benzenesulfinyl piperidine and triflic anhydride, in conjunction with an aqueous workup, hydrolyses a broad range of dithioacetals to the corresponding carbonyl compounds under very mild, non-oxidative conditions.

Key words

acetals - aldehydes - hydrolyses - ketones - protecting groups

References

• 1 Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   3rd ed.:  Wiley; New York: 1999. 
• 2 Seebach D. Angew. Chem., Int. Ed. Engl.  1969,  8:  639 
• 3 Smith AB. Boldi AM. J. Am. Chem. Soc.  1997,  119:  6925 
• 4 Smith AB. Pitram SM. Org. Lett.  1999,  1:  2001 
• 5 Bulman Page C. van Niel MB. Prodger JC. Tetrahedron  1989,  45:  7643 
• 7 Crich D. Smith M. J. Am. Chem. Soc.  2001,  123:  9015 
• 8 Crich D. Smith M. Yao Q. Picione J. Synthesis  2001,  323 
• 9 Crich D. Smith M. J. Am. Chem. Soc.  2002,  124:  8867 
• 10 Crich D. Li H. J. Org. Chem.  2002,  67:  4640 
• 11 Crich D. de la Mora MA. Cruz R. Tetrahedron  2002,  58:  35 

6

Commercially available from www.Lakeviewsynthesis.com.