Highly stereoselective Cope rearrangements of enantiomerically pure, silylated syn-aldols

Tetrahedron

Volumn 53, Issue 1, 1997, Pages 133-144

  Schneider, Christoph ^a   Rehfeuter, Markus ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031060190     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00958-1     Document Type: Article

References (25)

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2. Hill, R. K. in Comprehensive Organic Synthesis, VoL 5 (Eds.: Trost, B. M.; Fleming, I.), Pergamon, Oxford, 1991, p. 785; Wipf, P. ibid., p. 827; Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17.
3. Hill, R. K. in Comprehensive Organic Synthesis, VoL 5 (Eds.: Trost, B. M.; Fleming, I.), Pergamon, Oxford, 1991, p. 785; Wipf, P. ibid., p. 827; Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17.
4. Most recent work: Ireland, R. E.; Wipf, P.; Xiang, J. N. J. Org. Chem. 1991, 56, 3572; Corey, E. J.; Lee, D.H. J. Am. Chem. Soc. 1991, 113, 4026; Denmark, S. E.; Stadler, H.; Dorow, R. L.; Kim, J. H. J. Org. Chem. 1991, 56, 5063; Kazmaier, U.; Krebs, A. Angew. Chemie Int. Ed. Engl. 1995, 34, 2012; Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165; Diederich, M.; Nubbemeyer, U. Chem. Eur. J. 1996, 2, 894.
5. Most recent work: Ireland, R. E.; Wipf, P.; Xiang, J. N. J. Org. Chem. 1991, 56, 3572; Corey, E. J.; Lee, D.H. J. Am. Chem. Soc. 1991, 113, 4026; Denmark, S. E.; Stadler, H.; Dorow, R. L.; Kim, J. H. J. Org. Chem. 1991, 56, 5063; Kazmaier, U.; Krebs, A. Angew. Chemie Int. Ed. Engl. 1995, 34, 2012; Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165; Diederich, M.; Nubbemeyer, U. Chem. Eur. J. 1996, 2, 894.
6. Most recent work: Ireland, R. E.; Wipf, P.; Xiang, J. N. J. Org. Chem. 1991, 56, 3572; Corey, E. J.; Lee, D.H. J. Am. Chem. Soc. 1991, 113, 4026; Denmark, S. E.; Stadler, H.; Dorow, R. L.; Kim, J. H. J. Org. Chem. 1991, 56, 5063; Kazmaier, U.; Krebs, A. Angew. Chemie Int. Ed. Engl. 1995, 34, 2012; Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165; Diederich, M.; Nubbemeyer, U. Chem. Eur. J. 1996, 2, 894.
7. Most recent work: Ireland, R. E.; Wipf, P.; Xiang, J. N. J. Org. Chem. 1991, 56, 3572; Corey, E. J.; Lee, D.H. J. Am. Chem. Soc. 1991, 113, 4026; Denmark, S. E.; Stadler, H.; Dorow, R. L.; Kim, J. H. J. Org. Chem. 1991, 56, 5063; Kazmaier, U.; Krebs, A. Angew. Chemie Int. Ed. Engl. 1995, 34, 2012; Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165; Diederich, M.; Nubbemeyer, U. Chem. Eur. J. 1996, 2, 894.
8. Most recent work: Ireland, R. E.; Wipf, P.; Xiang, J. N. J. Org. Chem. 1991, 56, 3572; Corey, E. J.; Lee, D.H. J. Am. Chem. Soc. 1991, 113, 4026; Denmark, S. E.; Stadler, H.; Dorow, R. L.; Kim, J. H. J. Org. Chem. 1991, 56, 5063; Kazmaier, U.; Krebs, A. Angew. Chemie Int. Ed. Engl. 1995, 34, 2012; Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165; Diederich, M.; Nubbemeyer, U. Chem. Eur. J. 1996, 2, 894.
9. Most recent work: Ireland, R. E.; Wipf, P.; Xiang, J. N. J. Org. Chem. 1991, 56, 3572; Corey, E. J.; Lee, D.H. J. Am. Chem. Soc. 1991, 113, 4026; Denmark, S. E.; Stadler, H.; Dorow, R. L.; Kim, J. H. J. Org. Chem. 1991, 56, 5063; Kazmaier, U.; Krebs, A. Angew. Chemie Int. Ed. Engl. 1995, 34, 2012; Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165; Diederich, M.; Nubbemeyer, U. Chem. Eur. J. 1996, 2, 894.
10. The few reported examples are restricted to anionic oxy-Cope rearrangements, see: Tomooka, K.; Wei, S. Y.; Nakai, T. Chem. Lett. 1991, 43; Wei, S. Y.; Tomooka, K.; Nakai, T. J. Org. Chem. 1991, 56, 5973; Paquette, L. A.; Maynard, G. D. J. Am.Chem. Soc. 1992, 114, 5018; Lee, E.; Lee, Y. R.; Moon, B.; Kwon, O.; Shim, M. S. J. Org. Chem. 1994, 59, 1444.
11. The few reported examples are restricted to anionic oxy-Cope rearrangements, see: Tomooka, K.; Wei, S. Y.; Nakai, T. Chem. Lett. 1991, 43; Wei, S. Y.; Tomooka, K.; Nakai, T. J. Org. Chem. 1991, 56, 5973; Paquette, L. A.; Maynard, G. D. J. Am.Chem. Soc. 1992, 114, 5018; Lee, E.; Lee, Y. R.; Moon, B.; Kwon, O.; Shim, M. S. J. Org. Chem. 1994, 59, 1444.
12. The few reported examples are restricted to anionic oxy-Cope rearrangements, see: Tomooka, K.; Wei, S. Y.; Nakai, T. Chem. Lett. 1991, 43; Wei, S. Y.; Tomooka, K.; Nakai, T. J. Org. Chem. 1991, 56, 5973; Paquette, L. A.; Maynard, G. D. J. Am.Chem. Soc. 1992, 114, 5018; Lee, E.; Lee, Y. R.; Moon, B.; Kwon, O.; Shim, M. S. J. Org. Chem. 1994, 59, 1444.
13. The few reported examples are restricted to anionic oxy-Cope rearrangements, see: Tomooka, K.; Wei, S. Y.; Nakai, T. Chem. Lett. 1991, 43; Wei, S. Y.; Tomooka, K.; Nakai, T. J. Org. Chem. 1991, 56, 5973; Paquette, L. A.; Maynard, G. D. J. Am.Chem. Soc. 1992, 114, 5018; Lee, E.; Lee, Y. R.; Moon, B.; Kwon, O.; Shim, M. S. J. Org. Chem. 1994, 59, 1444.
14. Schneider, C.; Rehfeuter, M. Synlett 1996, 212.
15. After the precedent had been established (ref. 4) and the work described in this paper had been finished Prof. Nakai, Tokyo, reported on his investigations of Cope rearrangements of aldol products with a camphor sultam as chiral auxiliary, Japanese German Joint Symposium, Göttingen, 29.6.1996.
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