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Assessing the utility of HAlCl2 derived vinylalanes for Michael addition

Willcox, Darren, Gondal, Humaira, Civit, Marc Garcia and Woodward, Simon 2014. Assessing the utility of HAlCl2 derived vinylalanes for Michael addition. Tetrahedron Letters 55 (10) , pp. 1720-1721. 10.1016/j.tetlet.2014.01.105

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Abstract

Rare alkenylalanes are prepared by Cp2TiCl2 or Cp*2ZrCl2 (Cp = η-C5H5; Cp* = η-C5Me5) catalysed addition of HAlCl2·(THF)2 to terminal alkynes (R1CCH; R1 = alkyl). Use of minimum head-volume sealed vials maximises the hydroalumination yields of volatile alkynes. Facile 1,4-addition of the resultant alkenylalanes to unsaturated malonates R2CHC(CO2R3)2 (R2 = alkyl, aryl, R3 = alkyl) is observed providing rapid and convenient access to the addition products.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: Elsevier
ISSN: 0040-4039
Date of Acceptance: 22 January 2014
Last Modified: 04 Apr 2020 01:24
URI: http://orca.cardiff.ac.uk/id/eprint/122905

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