Conjugate addition of silyl groups to β-unsubstituted enones, and Si-to-OH conversion: A synthesis of (±)-lavandulol

Tetrahedron Letters

Volumn 37, Issue 38, 1996, Pages 6929-6930

  Fleming, Ian ^a   Lee, Duckhee ^a  

^a Department of Chemistry ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LAVANDULOL; TERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030590402     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01519-5     Document Type: Article

References (22)

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3. 2. Fleming, I.; Henning, R.; Plaut, H.; Parker, D. C.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317-337. For reviews of this reaction, see: Fleming, I. Chemtracts, Org. Chem. 1996, 9, 1-64.
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6. 2O, -78 °C, 0.5 h, r.t., 12 h, 70% after distillation, b.p. 149-155 °C/0.09 mmHg).
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8. 5. The usefulness of added trimethylsilyl chloride in cuprate conjugate additions is well established for carbon-cuprates: Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015. Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047. Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27. Bergdahl, M.; Linstedt, E.-L.; Nilsson, M.; Olsson, T. Tetrahedron 1988, 44, 2055. Matsuzawa, S.; Horiguchi, Y.; Nakamura, E.; Kuwajima, I. Tetrahedron 1989, 45, 349. Bergdahl, M.; Eriksson, M.; Nilsson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238. Nakamura, E., in Organocopper Reagents, ed. R. J. K. Taylor, OUP, Oxford, 1994.
9. 5. The usefulness of added trimethylsilyl chloride in cuprate conjugate additions is well established for carbon-cuprates: Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015. Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047. Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27. Bergdahl, M.; Linstedt, E.-L.; Nilsson, M.; Olsson, T. Tetrahedron 1988, 44, 2055. Matsuzawa, S.; Horiguchi, Y.; Nakamura, E.; Kuwajima, I. Tetrahedron 1989, 45, 349. Bergdahl, M.; Eriksson, M.; Nilsson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238. Nakamura, E., in Organocopper Reagents, ed. R. J. K. Taylor, OUP, Oxford, 1994.
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