Highly stereoselective intermolecular oxy-michael addition reaction to α,β-unsaturated malonate esters

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1357-1360

  Buchanan, David J ^a   Dixon, Darren J ^a   Hernandez Juan, Felix A ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ESTER DERIVATIVE; LACTONE DERIVATIVE; MALONIC ACID DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 2442462280     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049820x     Document Type: Article

References (16)

1. Reviews: (a) Misra, M.; Luthra, R.; Singh, K. L.; Sushil, K. In Comprehensive Natural Products Chemistry; Barton, D. H. R., Nakunisha, K., Meth-Chon, O., Eds.; Pergamon: Oxford, UK, 1999; Vol. 4. p 25. (b) Staunton, J.; Wilkinson, B. Top. Curr. Chem. 1998, 795, 49.
2. Reviews: (a) Misra, M.; Luthra, R.; Singh, K. L.; Sushil, K. In Comprehensive Natural Products Chemistry; Barton, D. H. R., Nakunisha, K., Meth-Chon, O., Eds.; Pergamon: Oxford, UK, 1999; Vol. 4. p 25. (b) Staunton, J.; Wilkinson, B. Top. Curr. Chem. 1998, 795, 49.
3. (a) Adderley, N. J.; Buchanan, D. J.; Dixon, D. J.; Lainé, D. I. Angew. Chem., Int. Ed. 2003, 35, 4241-4244.
4. (b) Buchanan, D. J.; Dixon, D. J.; Scott, M. S.; Laine, D. I. Tetrahedron: Asymmetry 2004, 75, 195-197.
5. (a) Enders, D.; Haertwig, A.; Raabe, G.; Runsink, J. Angew. Chem., Int. Ed. 1996, 35, 2388-2390.
6. (b) Enders, D.; Haertwig, A.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 1998, 1771-1792.
7. (c) Enders, D.; Haertwig, A.; Runsink, J. Eur. J. Org. Chem. 1998, 1793-1801.
8. For diastereoselective/nonenantioselective additions to nitro olefin acceptors, see: (a) Dumez, E.; Faure, R.; Dulcère, J.-P. Eur. J. Org. Chem. 2001, 2577-2588. (b) Yakura, T.; Tsuda, T.; Matsumura, Y.; Yamada, S.; Ikeda, M. Synlett 1996, 985-986.
9. For diastereoselective/nonenantioselective additions to nitro olefin acceptors, see: (a) Dumez, E.; Faure, R.; Dulcère, J.-P. Eur. J. Org. Chem. 2001, 2577-2588. (b) Yakura, T.; Tsuda, T.; Matsumura, Y.; Yamada, S.; Ikeda, M. Synlett 1996, 985-986.
10. For nonenantioselective additions of oxygen-centered nucleophiles to benzylidene(or alkylidene)malonates and related Michael acceptors, see: (a) Cavicchioli, M.; Marat, X.; Monteiro, N.; Hartmann, B.; Balme, G. Tetrahedron Lett. 2002, 43, 2609-2611. (b) Marat, X.; Monteiro, N.; Balme, G. Synlett 1997, 845-847. (c) Monteiro, N.; Balme, G. J. Org. Chem. 2000, 65, 3223-3226.
11. For nonenantioselective additions of oxygen-centered nucleophiles to benzylidene(or alkylidene)malonates and related Michael acceptors, see: (a) Cavicchioli, M.; Marat, X.; Monteiro, N.; Hartmann, B.; Balme, G. Tetrahedron Lett. 2002, 43, 2609-2611. (b) Marat, X.; Monteiro, N.; Balme, G. Synlett 1997, 845-847. (c) Monteiro, N.; Balme, G. J. Org. Chem. 2000, 65, 3223-3226.
12. For nonenantioselective additions of oxygen-centered nucleophiles to benzylidene(or alkylidene)malonates and related Michael acceptors, see: (a) Cavicchioli, M.; Marat, X.; Monteiro, N.; Hartmann, B.; Balme, G. Tetrahedron Lett. 2002, 43, 2609-2611. (b) Marat, X.; Monteiro, N.; Balme, G. Synlett 1997, 845-847. (c) Monteiro, N.; Balme, G. J. Org. Chem. 2000, 65, 3223-3226.
13. For asymmetric diastereoselective substrate-controlled additions of achiral oxygen-centered nucleophiles, see, for example: Paquette, L. A.; Tae, J.; Arlington, M. P.; Sadoun, A. H. J. Am. Chem. Soc. 2000, 122, 2742-2748.
14. For an interesting (nonenantioselective) synthesis of tetrahydrofurans using an oxy-Michael/Michael cyclization strategy, see: Greatrex, B. W.; Kimber, M. C.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2003, 68, 4239-4246.
15. Readily synthesized by condensation, see: Trost, B. M.; Higuchi, R. I. J. Am. Chem. Soc. 1996, 118, 10094-10105.
16. 1H NMR resonances of the minor diastereoisomer originating from the β-stereocenter of the cis-THP* adducts in the "selective" reaction.