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Organoboranes for Synthesis. 15. B-Allenyl-9-BBN: A Highly Regiospecific and Chemoselective Reagent for Allenylboration of Representative Carbonyl Compounds, …

…, UR Khire, G Narla, US Racherla

文献索引:Brown, Herbert C.; Khire, Uday R.; Narla, Gowriswari; Racherla, Uday S. Journal of Organic Chemistry, 1995 , vol. 60, # 3 p. 544 - 549

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被引用次数: 42

摘要

Reactions of B-allenyl-9-BBN (11) with representative carbonyl compounds, such as aldehydes, ketones, acid chlorides, carboxylic acid esters, and imines, proceed cleanly with the allenyl moiety undergoing transfer to the carbonyl or imine carbon, with allenic to propargylic rearrangement, and the boron moiety to the carbonyl oxygen or imine nitrogen. A simple oxidation with alkaline hydrogen peroxide results in the formation of the ...