Efficient synthesis of (R)-4-((trimethylsilyl)oxy)-2-cyclopentenone by enantioselective catalytic epoxide ring opening

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 389-390

  Leighton, James L ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030070775     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951557d     Document Type: Article

References (14)

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4. (d) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533-1564.
5. (a) Noyori, R.; Suzuki, M. Chemtracts:-Org. Chem. 1990, 3, 173-197.
6. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; pp 298-322.
7. For examples of recent applications of the three-component coupling approach, see: (a) Sato, T.; Shima, H.; Otera, J. J. Org. Chem. 1995, 60, 3936-3937. (b) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1994, 116, 11689-11702.
8. For examples of recent applications of the three-component coupling approach, see: (a) Sato, T.; Shima, H.; Otera, J. J. Org. Chem. 1995, 60, 3936-3937. (b) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1994, 116, 11689-11702.
9. See: Paquette, L. A.; Earle, M. J.; Smith, G. F. Org. Synth. 1995, 73, 36 and references therein.
10. Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898.
11. Suzuki, M.; Oda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623-1625.
12. 2.
13. Separation of 4 from 3, or analysis of the enantiomeric composition of 4 generated in the epoxide ring-opening reaction, proved impossible because of the extreme propensity of 3 to undergo elimination to generate 4.
14. Gill, M.; Rickards, R. W. Tetrahedron Lett. 1979, 1539-1542.