RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
          
          https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
        Synlett  2004(10): 1802-1804  
DOI: 10.1055/s-2004-829550
   DOI: 10.1055/s-2004-829550
LETTER
© Georg Thieme Verlag Stuttgart · New YorkLithium Hexafluorophosphate-Catalyzed Efficient Tetrahydropyranylation of Tertiary Alcohols under Mild Reaction Conditions
Weitere Informationen
            
               
                  
                        
                              Received
                              26 March 2004 
                      
Publikationsdatum:
15. Juli 2004 (online)
            
         
      
   Publikationsverlauf
Publikationsdatum:
15. Juli 2004 (online)

Abstract
Lithium hexafluorophosphate is found to be an efficient catalyst for the tetrahydropyranylation of tertiary alcohols with dihydropyran under mild reaction conditions.
Key words
alcohols - Lewis acids - lithium hexafluorophosphate - protecting groups - tetrahydropyranylation
- 1a 
             
            Reese CB. In Protective Groups in Organic ChemistryMcOmie JFW. Plenum; London: 1973. Chap. 3.Reference Ris Wihthout Link
- 1b 
             
            Kocienski PJ. In Protecting Groups Thieme; New York: 1994. Chap. 2.Reference Ris Wihthout Link
- 1c 
             
            Greene TW.Wuts PGM. In Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999. Chap. 2.Reference Ris Wihthout Link
- 2 
             
            Robertson DN. J. Org. Chem. 1960, 25: 931
- 3 
             
            Miyashita M.Yoshikoshi A.Grieco PA. J. Org. Chem. 1977, 42: 3772
- 4 
             
            Watahiki T.Kikumoto H.Matsuzaki M.Suzuki T.Oriyama T. Bull. Chem. Soc. Jpn. 2002, 75: 367
- 5 
             
            Mineno T. Tetrahedron Lett. 2002, 43: 7975
- 6 
             
            Kumar HMS.Reddy BVS.Reddy EJ.Yadav JS. Chem. Lett. 1999, 857
- 7 
             
            Stephens JR.Butler PL.Clow CH.Oswald MC.Smith RC.Mohan RS. Eur. J. Org. Chem. 2003, 3827
- For recent leading references, see:
- 8a 
             
            Yadav JS.Reddy BVS.Gnaneshwar D. New J. Chem. 2003, 27: 202
- 8b 
             
            Khan AT.Mondal E.Borah BM.Ghosh S. Eur. J. Org. Chem. 2003, 4113
- 8c 
             
            Wang R.Yang L.-M.Suo J.-S. Synth. Commun. 2003, 33: 3929 ; and references cited therein
- 9a 
             
            Babu BS.Balasubramanian KK. Synlett 1999, 1261
- 9b 
             
            Kazemi F.Kiasat AR.Ebrahimi S. Synth. Commun. 2002, 32: 2483
- 10 
             
            Karimi B.Maleki J. Tetrahedron Lett. 2002, 43: 5353
- 11 
             
            Babu BS.Balasubramanian KK. Tetrahedron Lett. 1998, 39: 9287
- 12 
             
            Reddy MA.Reddy LR.Bhanumathi N.Rao KR. Synth. Commun. 2000, 30: 4323
- 13a 
             
            Sumida N.Nishioka K.Sato T. Synlett 2001, 1921
- 13b 
             
            Nakae Y.Kusaki I.Sato T. Synlett 2001, 1584
- 13c 
             
            Ono F.Negoro R.Sato T. Synlett 2001, 1581
- A literature search shows that applications of LiPF6 in organic synthesis are rather rare. To the best of our knowledge it has been used only
- 14a for the oxidation of alcohols by a combination of cobalt-nitro complexes, see:  
            Tovrog BS.Diamond SE.Mares F.Szalkiewicz A. J. Am. Chem. Soc. 1981, 103: 3522
- 14b For the Diels-Alder reaction between 9,10-dimethylanthracene and acrylonitrile, see:
             
            Forman MA.Dailey WP. J. Am. Chem. Soc. 1991, 113: 2761
- For recent reports on other catalysts used to prepare tertiary alkyl THP ethers, see:
- 19a  
            Ref. 7 
- 19b  
            Ref. 8a 
- 19c  
            Ref. 8c 
- 19d 
             
            Bandgar BP.Sadavarte VS.Uppalla LS.Patil SV. Monatsh. Chem. 2003, 134: 425
- 19e  
            Ref. 4 
- 19f  
            Ref. 9b and references cited therein. 
- 19g  
            Ref. 10 
- 19h 
             
            Palaniappan S.Ram MS.Amarnath CA. Green Chem. 2002, 4: 369
- 19i 
             
            Gajare AS.Sabde DP.Shingare MS.Wakharkar RD. Synth. Commun. 2002, 32: 1549
- 19j 
             
            Namboodiri VV.Varma RS. Tetrahedron Lett. 2002, 43: 1143
References
The use of KPF6 instead of LiPF6 did not affect the protection at all.
16The Lewis acidity of lithium ion decreases when lithium ion is stabilized by coordinative solvation.
17Although testosterone is slightly soluble in hexane, quantitative tetrahydropyranylation was possible by using longer reaction times.
18Purchased from Kishida Chemical Co., Ltd.
 
    