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  2003(1): 0053-0062
DOI: 10.1055/s-2003-36256
   DOI: 10.1055/s-2003-36256
PAPER
© Georg Thieme Verlag Stuttgart · New YorkEnantiomerically Pure cis- and trans-2-Substituted Cyclopropanols from Allylic Sulfones
Further Information
            
               
                  
                        
                              Received
                              24 July 2002 
                      
Publication Date:
18 December 2002 (online)
            
         
      
   Publication History
Publication Date:
18 December 2002 (online)

Abstract
Enantiomerically pure cis- and trans-2-substituted cyclopropanols have been obtained from allylic sulfones derived from (R)-glyceraldehyde, in good yields.
Key words
cyclopropanols - sulfones - cyclization - synthesis
- 1 
             
            Kazuta Y.Matsuda A.Shuto S. J. Org. Chem. 2002, 67: 1669 ; and references cited therein
- 2a 
             
            Donaldson WA. Tetrahedron 2001, 57: 8589 ; and references cited therein
- 2b 
             
            Esposito A.Taddei M. J. Org. Chem. 2000, 65: 9245
- For asymmetric synthesis of disubstituted cyclopropanols in enantiomerically pure form from boronic esters see:
- 3a 
             
            Pietruszka J.Widenmeyer M. Synlett 1997, 977
- 3b 
             
            Fontani P.Carboni B.Vaultier M.Maas G. Synthesis 1991, 605
- 3c 
             
            Imai T.Mineta H.Nishida S. J. Org. Chem. 1990, 55: 4986
- 3d 
             
            Pietruszka J.Witt A. J. Chem. Soc., Perkin Trans. 1 2000, 4293
- 3e 
             
            Luithle JEA.Pietruszka J.Witt A. Chem. Commun. 1998, 2651
- 3f 
             
            Taylor RE.Schmidt MJ.Yuan H. Org. Lett. 2000, 2: 601 ; and references cited therein
- 3g 
             
            Baird MS.Huber AM.Clegg W. Tetrahedron 2001, 57: 9849
- For lead references, see
- 4a 
             
            Salaün J. The Chemistry of the Cyclopropyl Group, In Rearrangements Involving the Cyclopropyl GroupRappoport Z. Wiley; New York: 1987. p.809Reference Ris Wihthout Link
- 4b 
             
            de Meijere A. Carbocyclic Three and Four-membered Ring Systems in Methods of Organic Chemistry (Houben∠Weyl) Vol. E 17a∠f: Thieme; New York: 1997.Reference Ris Wihthout Link
- 4c 
             
            Sylvestre I.Olivier J.Salaün J. Tetrahedron Lett. 2001, 42: 4991 ; and references cited thereinReference Ris Wihthout Link
- 4d 
             
            Shaffer CL.Morthon MD.Hanzlik RP. J. Am. Chem. Soc. 2001, 123: 8502Reference Ris Wihthout Link
- 4e 
             
            Kulinkovich OG.de Meijere A. Chem. Rev. 2000, 100: 2789 ; and references cited thereinReference Ris Wihthout Link
- 5a 
             
            Díez D.San Feliciano SG.Marcos IS.Basabe P.Garrido NM.Urones JG. Synthesis 2001, 1069
- 5b 
             
            Díez D.Templo Beneitez M.Marcos IS.Garrido NM.Basabe P.Urones JG. Synlett 2001, 655
- 6 
             
            Díez D.Garcia P.Pacheco MP.Marcos IS.Garrido NM.Basabe P.Urones JG. Synlett 2002, 355
- 7 
             
            Kociénski PJ. In Protecting Groups Georg Thieme Verlag; Stuttgart and New York: 1994.Reference Ris Wihthout Link
- 8a 
             
            Reissig H.-U.Böhn I. J. Am. Chem. Soc. 1982, 104: 1735
- 8b 
             
            Padwa A.Wannamaker MW. Tetrahedron Lett. 1986, 27: 2555
- 8c 
             
            Militzer H.-C.Schömenauer S.Otte C.Puls C.Hain JBS.de Meijere A. Synthesis 1993, 998 ; and references cited therein
 
    