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), pp. 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
Digital Object Identifier (DOI): doi:10.1016/S0040-4039(02)02857-5
ISSNs: 0040-4039 (print)
Keywords: alpha, beta-unsaturated ketones, reagents, transmetalation, enones
Subjects:
ePrint ID: 19939
Date :
Date Event
10 February 2003Published
Date Deposited: 17 Feb 2006
Last Modified: 16 Apr 2017 23:00
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/19939

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