Pyridinium Ylides in the Synthesis of 2,3-Dihydrofurans

Abstract

A new method for the synthesis of 2,3-dihydrofurans from readily available starting enones and pyridinium salts has been developed. This protocol can provide a novel and effective methodology for the preparation of 2,3-dihydrofurans in a stereoselective fashion. To increase the efficiency of this reaction the one-pot process was also developed, in which the pyridinium salts were generated in situ from corresponding halides.

Key words

pyridinium ylide - 2,3-dihydrofuran - conjugate addition - O-cyclization - one-pot process

References

• 1a Dean FM. Sargent MV. In Comprehensive Heterocyclic Chemistry   Vol. 4:  Bird CW. Cheeseman GWH. Pergamon Press; New York: 1984.  Part 3. p.531 
• 1b Lipshutz BH. Chem. Rev.  1986,  86:  795 
• 2a Heiba EI. Dessau RM. J. Org. Chem.  1974,  39:  3456 
• 2b Baciocchi E. Ruzziconi R. Synth. Commun.  1988,  18:  1841 
• 2c Nair V. Mathew J. Radhakrishnan KV. J. Chem. Soc., Perkin Trans. 1  1996,  1487 
• 2d Nair V. Mathew J. Nair LG. Synth. Commun.  1996,  26:  4531 
• 2e Roy SC. Mandal PK. Tetrahedron  1996,  52:  2193 
• 2f Roy SC. Mandal PK. Tetrahedron  1996,  52:  12495 
• 2g Lee YR. Kim NS. Kim BS. Tetrahedron Lett.  1997,  38:  5671 
• 2h Lee YR. Kim BS. Wang HC. Tetrahedron  1998,  54:  12215 
• 2i Bar G. Parson AF. Thomas CB. Tetrahedron Lett.  2000,  41:  7751 
• 2j Zhang Y. Raines AJ. Flowers RA. Org. Lett.  2003,  5:  2363 
• 3a Jaxa-Chamiec AA. Sammes PG. J. Chem. Soc., Perkin Trans. 1  1980,  170 
• 3b Arai S. Nakayama K. Suzuki T. Hatano K. Shioiri T. Tetrahedron Lett.  1998,  39:  9739 
• 3c Dyker G. Thöne A. Tetrahedron  2000,  56:  8669 
• 3d Antonioletti R. Malancona S. Bovicelli P. Tetrahedron  2002,  58:  8825 
• 3e Calò V. Scordari F. Nacci A. Schinggaro E. D’Accolti L. Monopoli A. J. Org. Chem.  2003,  68:  4406 
• 4a Zhang X. Cao W. Wei X. Hu H. Synth. Commun.  1997,  27:  1395 
• 4b Zhang X. Huang W. J. Fluorine Chem.  1998,  92:  13 
• 4c Zhu S. Qin C. Wang Y.-L. Chu Q. J. Fluorine Chem.  1999,  99:  183 
• 4d Wang B. Zhang X. Li J. Jiang X. Hu Y. Hu H. J. Chem. Soc., Perkin Trans. 1  1999,  1571 
• 4e Miki Y. Nakamura N. Yamakawa R. Hachiken H. Matsushita K. Heterocycles  2000,  53:  2143 
• 4f Bora U. Saikia A. Boruah RC. Org. Lett.  2003,  5:  435 
• 5a Kröhnke F. Zecher W. Curtze J. Drechsler D. Pfleghar K. Schnalke KE. Weis W. Angew. Chem.  1962,  74:  811 
• 5b Bansal RK. Sharma D. Jain JK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1988,  27:  366 
• 5c Kumar A. Rhodes RA. Spychala J. Wilson WD. Boykin DW. Tidwell RR. Dykstra CC. Hall JE. Jones SK. Schinazi RF. Eur. J. Med. Chem.  1995,  30:  99 
• 5d Katoh A. Kitamura Y. Fujii H. Horie Y. Satoh T. Ohkanda J. Yokomori Y. Heterocycles  1998,  49:  281 
• Similar 3-membered ring C-cyclization of ylides has been reported. See:
• 6a Moorhoff CM. Tetrahedron Lett.  1996,  37:  9349 
• 6b Vo NH. Eyermann CJ. Hodge CN. Tetrahedron Lett.  1997,  38:  7951 
• 6c Papageorgiou CD. Ley SV. Gaunt MJ. Angew. Chem. Int. Ed.  2003,  42:  828 
• 7 Tsuge O. Kanemasa S. Takenaka S. Bull. Chem. Soc. Jpn.  1985,  58:  3137