Conjugate additions of lithium dialkynylcuprates (RC C)(2)CuLi to activated chromones. Unexpected formation of the 6H-bis 1 benzopyrano 2,3-b : 3',4'-e pyridine system


Daia, D. E., Gabbutt, C. D., Heron, B. M., Hepworth, J. D., Hursthouse, M. B. and Malik, K. M. A. (2003) Conjugate additions of lithium dialkynylcuprates (RC C)(2)CuLi to activated chromones. Unexpected formation of the 6H-bis 1 benzopyrano 2,3-b : 3',4'-e pyridine system. Tetrahedron Letters, 44, (7), 1461-1464. (doi:10.1016/S0040-4039(02)02857-5).

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Description/Abstract

Lithium dialkynylcuprates [(RCequivalent toC)(2)CuLi], 1a-d, are easily generated and undergo conjugate additions to activated chromones giving 2-alkynylchroman-4-ones 4a-d, 13, 15c,d and 5, however, 1,4-additions to 3 proceed anomalously to give the eneynonitriles 6a-b and the bisbenzopyranopyridine 7.

Item Type: Article
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Keywords: alpha,beta-unsaturated ketones, reagents, transmetalation, enones
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 19939
Date Deposited: 17 Feb 2006
Last Modified: 27 Mar 2014 18:09
URI: http://eprints.soton.ac.uk/id/eprint/19939

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