Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
          
          https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
        Synlett  2004(3): 564-571  
DOI: 10.1055/s-2004-815435
   DOI: 10.1055/s-2004-815435
NEWTOOLS
© Georg Thieme Verlag Stuttgart · New YorkVilsmeier-Haack Reagents. Novel Electrophiles for the One-Step Formylation of O-Silylated Ethers to O-Formates
Further Information
            
               
                  
                        
                              Received
                              30 October 2003 
                      
Publication Date:
26 January 2004 (online)
            
         
      
   Publication History
Publication Date:
26 January 2004 (online)

Abstract
Various O-silylated substrates were effectively converted in one-step to their corresponding O-formates using electrophilic racemic and homochiral Vilsmeier-Haack reagents. Reactivity trends of these transformations were examined that, specifically, emphasized their synthetic potential.
Key words
Vilsmeier-Haack complexes - deprotection of O-silyl ethers - one-step deprotection - preparation of O-formates - formyl glycosides
- 1 
             
            Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd Ed.: John Wiley and Sons Inc.; New York: 1999.Reference Ris Wihthout Link
- 2 
             
            Kocie PJ. Protecting Groups Georg Thieme Verlag; Stuttgart: 1994.ski Reference Ris Wihthout Link
- 3 
             
            Prakash C.Saleh S.Blair IA. Tetrahedron Lett. 1994, 35: 7565
- 4 
             
            Maiti G.Roy SC. Tetrahedron Lett. 1997, 38: 495
- 5a 
             
            Kim S.Lee WJ. Synth. Commun. 1986, 16: 659
- 5b 
             
            Oriyama T.Oda M.Gono J.Koga G. Tetrahedron Lett. 1994, 35: 2027
- 5c 
             
            Ganem B.Small RV. J. Org. Chem. 1974, 39: 3728
- 5d 
             
            Oriyama T.Noda K.Yatabe K. Synlett 1997, 701
- 5e 
             
            Chandra KL.Saravanan P.Singh VK. Tetrahedron Lett. 2001, 42: 5309
- 5f 
             
            Sharma GVM.Mahalingam AK.Nagarajan M.Ilangovan A.Radhakrishna P. Synlett 1999, 1200
- 5g 
             
            Reddy CS.Smitha G.Chandrasekhar S. Tetrahedron Lett. 2003, 44: 4693
- 6 
             
            Saunders DG. Synthesis 1988, 377
- 7 
             
            Suzuki T.Oriyama T. Synthesis 2001, 555
- 8 
             
            Marson CM. Tetrahedron 1992, 48: 3659
- 9 
             
            Marson CM.Giles PR. Synthesis Using Vilsmeier Reagents CRC Press; Boca Raton: 1994.Reference Ris Wihthout Link
- 10 
             
            Koeller S.Lellouche J.-P. Tetrahedron Lett. 1999, 40: 7043
- 11 
             
            Lellouche J.-P.Koeller S. J. Org. Chem. 2001, 66: 693
- 12 
             
            Martinez AG.Alvarez RM.Barcina JO.de la Moya Cerero S.Vilar ET.Fraile AG.Hanack M.Subramanian LR. J. Chem. Soc., Chem. Commun. 1990, 1571
- 13 
             
            Ramesh NG.Balasubramanian KK. Tetrahedron Lett. 1991, 32: 3875
- 14 
             
            Lide DR. Handbook of Chemistry and Physics 8th Ed.: CRC Press; Boca Raton: 1997. p.9/667Reference Ris Wihthout Link
- 15 
             
            Friesen RW.Danishefsky SJ. J. Am. Chem. Soc. 1989, 11: 6656
- 16 
             
            Danishefsky SJ.Bilodeau MT. Angew. Chem., Int. Ed. Engl. 1996, 35: 1381
- 17 
             
            Cohen Y. MSc Thesis Bar-Ilan University; Ramat-Gan Israel: 2002.Reference Ris Wihthout Link
- 18a 
             
            Bols M.Skrydstrup T. Chem. Rev. 1995, 95: 1253
- 18b 
             
            Fensterbank L.Malacria M.Sieburth S. Synthesis 1997, 813
- 18c 
             
            Gauthier DR.Zandi KS.Shea KJ. Tetrahedron 1998, 54: 228
- 19 
             
            Cohen Y.Kotlyar V.Koeller S.Lellouche J.-P. Synlett 2001, 1543
- 20 
             
            Chmurski K.Defaye J. Tetrahedron Lett. 1997, 42: 7365
- 21a 
             
            Khan AR.D’Souza VT. J. Org. Chem. 1994, 59: 7492
- 21b 
             
            Benazza M.Massoui M.Uzan R.Demailly G. Carbohydr. Res 1995, 275: 421
- 21c 
             
            Benazza M.Beaupere D.Uzan R.Demailly G. Carbohydr. Res. 1991, 218: 75
- 22 
             
            Djuric SW. J. Org. Chem. 1984, 49: 1311
- 23 
             
            Hodosi G.Podanyi B.Kuszmann J. Carbohydr. Res. 1992, 230: 327
- 24a 
             
            Gorin BI.Riopelle RJ.Thatcher GRJ. Tetrahedron Lett. 1996, 37: 4647
- 24b 
             
            Baer HH.Berenguel AV.Shu YY. Carbohydr. Res. 1992, 228: 307
- 24c 
             
            Gadelle A.Defaye J. Angew. Chem. Int. Ed. Engl. 1991, 30: 78
- 25 
             
            Barluenga J.Campos PJ.Gonzalez-Nunez E.Asensio G. Synthesis 1985, 426
- 26 
             
            De Luca L.Giacomelli G.Porcheddu A. Org. Lett. 2002, 4: 553
 
    