CuCN-mediated intramolecular conjugate additions. Syntheses of functionalized, cis-fused bicyclo[6.3.0]undecanes, bicyclo[6.4.0]dodecanes, and bicyclo[7.4.0]tridecanes

Synlett

Volumn , Issue 12, 1999, Pages 1867-1870

  Piers, Edward ^a   Skupinska, Krystyna A ^a   Wallace, Debra J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

(alkenyl)trimethylstannanes; Aldol condensation; Alkylation; Copper(I) cyanide; Medium size carbocycles; Ruthenium tetroxide

Indexed keywords

COPPER DERIVATIVE; CYANIDE; RUTHENIUM DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; POLYMERIZATION; SYNTHESIS;

EID: 0032757230     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2986     Document Type: Article

References (16)

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11. Piers, E.; Romero, M. A. J. Am. Chem. Soc. 1996, 118, 1215.
12. The enolate of 1 was prepared in THF (-78 → 0 °C) and the alkylation was carried out in the presence of HMPA (-78 → 0 °C). For the alkylation of 2, the corresponding temperatures were -78 °C → room teperature, and no HMPA was used.
13. All compounds reported herein exhibit spectra in accord with structural assignments and new compounds gave satisfactory elemental analyses and (or) high resolution mass spectrometric molecular mass determinations.
14. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 45, 3936.
15. Mehta, G.; Murty, A. N. J. Org. Chem. 1990, 55, 3568.
16. These X-ray analyses were carried out by Dr. S. J. Rettig (deceased October 27, 1998), Professional Officer, UBC X-ray Crystal Structure Laboratory. Details of these structure determinations will be reported elsewhere.