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        Synthesis  2010(9): 1493-1499  
DOI: 10.1055/s-0029-1218693
   DOI: 10.1055/s-0029-1218693
PAPER
© Georg Thieme Verlag
      Stuttgart ˙ New YorkChemoselective (Trans)thioacetalization of Carbonyl Compounds with a Reusable Lewis Acid-Surfactant-Combined Copper Bis(dodecyl sulfate) Catalyst in Water
Weitere Informationen
            
               
                  
                        
                              Received
                              8 December 2009 
                      
Publikationsdatum:
09. März 2010 (online)
            
         
      
   Publikationsverlauf
Publikationsdatum:
09. März 2010 (online)
Abstract
A Lewis acid-surfactant-combined copper bis(dodecyl sulfate) [Cu(DS)2] catalyst served as an efficient and reusable catalyst for the thioacetalization and transthioacetalization of carbonyl compounds and O,O-acetals in water at room temperature. Some of the major advantages of this procedure are high chemoselectivity, ease of operation and purification without any organic solvent, and high yields.
Key words
thioacetalization - transthioacetalization - Lewis acid-surfactant-combined catalysts - copper bis(dodecyl sulfate) - reusability
- 1 
             
            
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley & Sons; New York: 1999. p.329 - 2a 
             
            
Corey EJ.Seebach D. Angew. Chem., Int. Ed. Engl. 1965, 4: 1075 - 2b 
             
            
Seebach D.Corey EJ. J. Org. Chem. 1975, 40: 231 - 2c 
             
            
Grobel BT.Seebach D. Synthesis 1977, 357 - 2d 
             
            
Seebach D. Angew. Chem., Int. Ed. Engl. 1979, 18: 239 - 2e 
             
            
Smith AB.Christopher MA. Acc. Chem. Res. 2004, 37: 365 - 3a 
             
            
Yus M.Nájera C.Foubelo F. Tetrahedron 2003, 59: 6147 - 3b 
             
            
Smith AB.Pitram SM.Gaunt MJ.Kozmin SA. J. Am. Chem. Soc. 2002, 124: 14516 - 3c 
             
            
Takeda T.Kuroi S.Yanai K.Tsubouchi A. Tetrahedron Lett. 2002, 43: 5641 - 3d 
             
            
Smith AB.Lin Q.Doughty VA.Zhuang L.McBriar MD.Kerns JK.Brook CS.Murase N.Nakayama K. Angew. Chem. Int. Ed. 2001, 40: 196 - 3e 
             
            
Breit B. Angew. Chem. Int. Ed. 1998, 37: 453 - 3f 
             
            
Horikawa Y.Watanabe M.Fujiwara T.Takeda T. J. Am. Chem. Soc. 1997, 119: 1127 - 4 
             
            
Truce WE.Roberts FE. J. Org. Chem. 1963, 28: 961 - 5 
             
            
Garlaschelli L.Vidari G. Tetrahedron Lett. 1990, 31: 5815 - 6 
             
            
Patney HK. Tetrahedron Lett. 1991, 32: 2259 - 7a 
             
            
Khan AT.Parvin T.Choudhury LH. Synthesis 2006, 2497 - 7b 
             
            
Kamitori T.Hojo K.Masuda R.Kimura T.Yoshida T. J. Org. Chem. 1986, 51: 1427 - 8a 
             
            
Patney HK.Margan S. Tetrahedron Lett. 1996, 37: 4621 - 8b 
             
            
Firouzabadi H.Iranpoor N.Karimi B. Synlett 1999, 319 - 9 
             
            
Anand R.Saravanan VP.Singh VK. Synlett 1999, 415 - 10 
             
            
Ong BS. Tetrahedron Lett. 1980, 21: 4225 - 11 
             
            
Tani H.Masumoto K.Inamasu T. Tetrahedron Lett. 1991, 32: 2039 - 12 
             
            
Das NB.Nayak A.Sharma RP. J. Chem. Res., Synop. 1993, 242 - 13 
             
            
Ku B.Oh DY. Synth. Commun. 1989, 19: 433 - 14 
             
            
Kumar V.Dev S. Tetrahedron Lett. 1983, 24: 1289 - 15a 
             
            
Muthusamy S.Babu SA.Gunanathan C. Tetrahedron Lett. 2001, 42: 359 - 15b 
             
            
Muthusamy S.Babu SA.Gunanathan C. Synth. Commun. 2001, 31: 1205 - 16 
             
            
Fieser LF. J. Am. Chem. Soc. 1954, 76: 1945 - 17 
             
            
Corey EJ.Shimoji K. Tetrahedron Lett. 1983, 24: 169 - 18a 
             
            
Firouzabadi H.Iranpoor N.Hazarkhani H. J. Org. Chem. 2001, 66: 7527 - 18b 
             
            
Deka N.Sarma JC. Chem. Lett. 2001, 749 ; and references cited therein - 19 
             
            
Perni RB. Synth. Commun. 1989, 19: 2383 - 20 
             
            
Saraswathy VG.Sankararaman S. J. Org. Chem. 1994, 59: 4665 - 21 
             
            
De S K. Synthesis 2004, 2837 - 22 
             
            
De S K. Tetrahedron Lett. 2004, 45: 1035 - 23 
             
            
Firouzabadi H.Iranpoor N.Karimi B. Synlett 1998, 739 - 24 
             
            
Kazahaya K.Tsuneo S.Sato T. Synlett 2004, 1640 - 25 
             
            
Kamal A.Chouhan G. Synlett 2002, 474 - 26a 
             
            
Kamal A.Chouhan G. Tetrahedron Lett. 2002, 43: 1347 - 26b 
             
            
Kamal A.Chouhan G. Tetrahedron Lett. 2003, 44: 3337 - 26c 
             
            
De S K. Synthesis 2004, 828 - 27 
             
            
De S K. J. Mol. Catal. A: Chem. 2005, 232: 77 - 28a 
             
            Organic Synthesis in Water
              
             
            
Grieco PA. Blackie Academic & Professional; London: 1998. - 28b 
             
            
Li C.-J.Chan T.-H. Organic Reactions in Aqueous Media Wiley & Sons; New York: 1997. - 28c 
             
            
Breslow R. Acc. Chem. Res. 1991, 24: 159 - 29a 
             
            
Manabe K.Sun X.-M.Kobayashi S. J. Am. Chem. Soc. 2001, 123: 10101 - 29b 
             
            
Manabe K.Iimura S.Sun X.-M.Kobayashi S. J. Am. Chem. Soc. 2002, 124: 11971 - 29c 
             
            
Mori Y.Manabe K.Kobayashi S. Angew. Chem. Int. Ed. 2001, 40: 2815 - 29d 
             
            
Kobayashi S.Manabe K. Acc. Chem. Res. 2002, 35: 209 ; and references cited therein - 30a 
             
            
Otto S.Engberts JBFN.Kwak JCT. J. Am. Chem. Soc. 1998, 120: 9517 - 30b 
             
            
Otto S.Engberts JBFN.Kwak JCT. J. Am. Chem. Soc. 1999, 121: 6798 - 31a 
             
            
Kobayashi S.Mori Y.Nagayama S.Manabe K. Green Chem. 1999, 1: 175 - 31b 
             
            
Manabe K.Mori Y.Kobayashi S. Synlett 1999, 1401 - 31c 
             
            
Manabe K.Kobayashi S. Org. Lett. 1999, 1: 1965 - 31d 
             
            
Manabe K.Mori Y.Kobayashi S. Tetrahedron 2001, 57: 2537 - 31e 
             
            
Akiyama T.Takaya J.Kagoshima H. Synlett 1999, 1426 - 32 
             
            
Ceschi M.Felix ALDA.Peppe C. Tetrahedron Lett. 2000, 41: 9695 - 33a 
             
            
Moroi Y.Motomura K.Matuura R. J. Colloid Interface Sci. 1974, 46: 111 - 33b 
             
            
Kamenka N.Burgaud I.Treiner C.Zana R. Langmuir 1994, 10: 3455 - 34a 
             
            
Satake I.Iwamatsu I.Hosokawa S.Matuura R. Bull. Chem. Soc. Jpn. 1963, 36: 204 - 34b 
             
            
Satake I.Matuura R. Bull. Chem. Soc. Jpn. 1963, 36: 813 - Several catalytic transthioacetalization systems are faster and more efficient than direct thioacetalization; see:
 - 35a 
             
            
Muthusamy A.Babu SA.Gunanathan C. Tetrahedron 2002, 58: 7897 - 35b 
             
            
Ranu BC.Das A.Samanta S. Synlett 2002, 727 - 36 
             
            
Sato T.Otera J.Nozaki H. J. Org. Chem. 1993, 58: 4971