Highly syn-diastereoselective synthesis of NH-3-benzyloxy-4-aryl-azetidin-2-ones via a two-step Staudinger reaction

Synlett

Volumn , Issue 8, 1998, Pages 843-844

  Bacchi, Sergio ^a   Bongini, Alessandro ^a   Panunzio, Mauro ^a   Villa, Marzia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000869472     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1793     Document Type: Article

References (17)

1. For a review see: Nicolaou, K.C.; Day, W.-M.; Guy, R.K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44.
2. Holton, R.A.; Kim, H.-B.; Somoza, C.; Liang, F.; Biediger, R.J.; Boatman, D.P.; Shindo, M.; Smith, C.C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N.; Liu, J.H. J. Am. Chem. Soc. 1994, 116, 1599-1600.
3. (b) Georg, G.I.; Harriman, G.C.B.; Hepperle, M.; Glowers, J.S.; Vander Velde, D.G. J. Org. Chem. 1996, 61, 2664-2676 and ref. therein cited.
4. For recent syntheses of phenylisoserine see: (a) Song, C.E.; Lee, S.W.; Roh, E.J.; Lee, S.; Lee, W.-K. Tetrahedron: Asymmetry 1998, 9, 983-992.
5. (b) Li, G.; Sharpless, K.B. Acta Chem. Scand. 1996, 50, 649-651 and references therein cited. See also ref. 5e.
6. (a) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; G. Georg, Ed.; VCH: New York, 1993; pp 318-323.
7. (b) Birkofer, L.; Schramm, J. Liebigs Ann. Chem. 1977, 760-766.
8. (c) Panunzio, M.; Cozzi, P.G.; Kretz, C.M.; Bandini, E.; Martelli, G. In Topics in Heterocyclic Systems- Synthesis, Reactions and Properties, Attanasi, A.O. and Spinelli, G. Eds.; Research Signpost, Trivandrum, 1996; pp 119-140.
9. (d) Colvin, E.W.; McGarry, D.; Nugent, J.M. Tetrahedron 1988, 44, 4157-4172.
10. (e) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, H.Y.; Sun, M.C.; Brigaud, T. Tetrahedron 1992, 48, 6985-7012.
11. (a) Bandini, E.; Martelli, G.; Spunta, G.; Bongini, A.; Panunzio, M., Tetrahedron Lett. 1996, 37, 4409-1412.
12. (b) Bandini, E.; Martelli, G.; Spunta, G.; Panunzio, M., Synlett 1996, 1017-1018.
13. (c) For preparation and application of N-trialkylsilylimines in organic synthesis see: Panunzio, M.; Zarantonello, P., Org. Process Res.Dev. 1998, 2, 49-59.
14. General procedure : To a solution of aldehyde 1 (1 mmol) in hexane (5 ml) was added LiHMDSA (1 mL of 1M solution in THF) at 0°C. The reaction mixture was allowed to reach r.t. spontaneously while the stirring was continued for 1 h. TMSCl (1.1 mmol) was added in one portion and the reaction mixture further stirred for 1 h. A white precipitate formed. The solution was cooled at 0°C and triethylamine (1 mmol) was added in one portion. The benzyloxyacetyl chloride 3 (1mmol), dissolved in toluene (3 mL), was added dropwise. Stirring was maintained for 1 h while a new copious precipitate appeared. The precipitate was filtered under argon, the solvent removed in vacuo, dichloromethane (10 mL) was added and the resulting pale yellow solution was stirred overnight at r.t. The crude mixture was poured into a 1 N HCl solution and extracted with ethyl acetate. Flash chromatography of the residue (cyclohexane/ethyl acetate 1/1) yielded the pure isolated cis-N-unsubstituted-3-benzyloxy-4-aryl-β-lactams 5 in the yields reported in Table 1.
15. Bose, A.K.; Chiang, Y.H.; Manhas, M.S. Tetrahedron Lett. 1972, 4091-4094.
16. (a) Manhas, M.S.; Amin, S.G.; Chawla, H.P.S.; Bose, A.K. J. Heterocycl. Chem. 1978, 15, 601.
17. (b) Brieva, R.; Crich, J.Z.; Sih, C.J. J. Org. Chem. 1993, 58, 1068-1075.