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-00000084.xml
        Synthesis  2005(9): 1421-1424  
DOI: 10.1055/s-2005-865312
   DOI: 10.1055/s-2005-865312
PAPER
© Georg Thieme Verlag Stuttgart · New YorkRing-Closing Metathesis (RCM) for the Synthesis of Cyclic Sulfoximines
Further Information
            
               
                  
                        
                              Received
                              9 February 2005 
                      
Publication Date:
12 April 2005 (online)
            
         
      
   Publication History
Publication Date:
12 April 2005 (online)

Abstract
Chiral heterocycles can be prepared starting from doubly unsaturated sulfoximine derivatives by ring-closing metathesis reaction in good yields.
Key words
catalysis - heterocycles - macrocycles - ring-closing metathesis - sulfoximines
- Reviews:
- 1a 
             
            Reggelin M.Zur C. Synthesis 2000, 1
- 1b 
             
            Mikolajczk M.Drabowicz J.Kielbasinski P. Chiral Sulfur Reagents CRC Press; Boca Raton: 1997.
- 1c 
             
            Pyne S. Sulfur Reports 1992, 12: 57
- 1d 
             
            Haake M. In Houben-Weyl Vol. E11: Klamann D., Thieme; Stuttgart: 1985. p.1299
- 1e 
             
            Johnson CR. Acc. Chem. Res. 1973, 6: 341
- 1f 
             
            Johnson CR. Aldrichimica Acta 1985, 18: 3
- For the use of sulfoximines as chiral ligands in asymmetric catalysis, see (reviews):
- 2a 
             
            Okamura H.Bolm C. Chem. Lett. 2004, 33: 482
- 2b 
             
            Harmata M. Chemtracts - Org. Chem. 2003, 16: 660
- 3a 
             
            Mock WL.Tsay J.-T. J. Am. Chem. Soc. 1989, 111: 4467
- 3b 
             
            Mock WL.Zhang JZ. J. Biol. Chem. 1991, 266: 6393
- 3c 
             
            Bolm C.Kahmann JD.Moll G. Tetrahedron Lett. 1997, 38: 1169
- 3d 
             
            Bolm C.Moll G.Kahmann JD. Chem. Eur. J. 2001, 7: 1118
- 3e 
             
            Tye H.Skinner CL. Helv. Chim. Acta 2002, 85: 3272
- 3f 
             
            Bolm C.Müller D.Hackenberger CPR. Org. Lett. 2002, 4: 893
- 3g 
             
            Bolm C.Müller D.Dalhoff C.Hackenberger CPR.Weinhold E. Bioorg. Med. Chem. Lett. 2003, 13: 3207
- 4a 
             
            Mellanby E. Br. Med. J. 1946, 2: 885
- 4b 
             
            Mellanby E. Br. Med. J. 1947, 3: 288
- 4c 
             
            Bentley HR.McDermott EE.Moran T.Pace J.Whitehead JK. Proc. Roy. Soc. B 1950, 137: 402
- For examples, see:
- 5a 
             
            Williams TR.Cram DJ. J. Org. Chem. 1973, 38: 20
- 5b 
             
            Stoss P.Satzinger G. Chem. Ber. 1972, 105: 2575
- 5c 
             
            Williams TR.Cram DJ. J. Am. Chem. Soc. 1971, 93: 7333
- 6a 
             
            Harmata M.Kahraman M.Jones DE.Pavri N.Weatherwax SE. Tetrahderon 1998, 54: 9995
- 6b 
             
            Harmata M.Pavri N. Angew. Chem. Int. Ed. 1999, 38: 2419
- 6c 
             
            Harmata M.Ghosh SK. Org. Lett. 2001, 3: 3321
- 6d 
             
            Harmata M.Hong X. J. Am. Chem. Soc. 2003, 125: 5754
- 6e 
             
            Harmata M.Rayanil K.-O.Gomes MG.Zheng P.Calkins NL.Kim S.-Y.Fan Y.Bumbu V.Lee DR.Wacharasindhu S.Hong X. Org. Lett. 2005, 7: 143 ; and references cited therein
- 7a 
             
            Bolm C.Martin M.Gibson L. Synlett 2002, 832
- 7b 
             
            Bolm C.Okamura H.Verrucci M. J. Organomet. Chem. 2003, 687: 444
- 8a 
             
            Schuster M.Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36: 2036Reference Ris Wihthout Link
- 8b 
             
            Grubbs RH.Chang S. Tetrahedron 1998, 54: 4413Reference Ris Wihthout Link
- 8c 
             
            Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012Reference Ris Wihthout Link
- 8d 
             
            Trnka TM.Grubbs RH. Acc. Chem. Res. 2001, 34: 18Reference Ris Wihthout Link
- 8e 
             
            Armstrong SK. J. Chem. Soc., Perkin Trans. 1 1998, 371Reference Ris Wihthout Link
- 8f 
             
            Schrock RR.Hoveyda AH. Angew. Chem. Int. Ed. 2003, 42: 4592Reference Ris Wihthout Link
- 8g 
             
            Yet L. Chem. Rev. 2000, 100: 2963Reference Ris Wihthout Link
- 8h 
             
            Handbook of Metathesis
              
            Grubbs R. H., Wiley-VCH; 
            Weinheim: 
            2003. and references cited therein
            
            Reference Ris Wihthout Link
- For other recent summaries of RCM reactions affording sulfur-containing heterocycles, see:
- 9a 
             
            Karsch S.Freitag D.Schwab P.Metz P. Synthesis 2004, 1696
- 9b 
             
            McReynolds MD.Dougherty JM.Hanson PR. Chem. Rev. 2004, 104: 2239
- In this study racemic sulfoximine 4 was used. However, since the preparation of 4 in both enantiomeric forms is well established, a ‘chiral switch’ should be easy to achieve. For key references describing the preparation of enantiopure 4, see:
- 10a 
             
            Fusco R.Tericoni F. Chem. Ind. (Milan) 1965, 47: 61
- 10b 
             
            Johnson CR.Schroeck CW. J. Am. Chem. Soc. 1973, 95: 7418
- 10c 
             
            Johnson CR.Schroeck CW.Shanklin JR. J. Am. Chem. Soc. 1973, 95: 7424
- 10d 
             
            Brandt J.Gais H.-J. Tetrahedron: Asymmetry 1997, 8: 909
- 12 
             
            Okamura H.Bolm C. Org. Lett. 2004, 6: 1305
- 13a 
             
            Bolm C.Hackenberger CPR.Simic O.Verrucci M.Müller D.Bienewald F. Synthesis 2002, 879
- 13b 
             
            Hackenberger CPR.Raabe G.Bolm C. Chem. Eur. J. 2004, 10: 2942
References
These products are shown with defined stereochemistry at the double bond, although it was not determined if an E or Z olefin was formed.
 
    