Stec, Jozef, Henderson, Alan R. and Whitby, Richard J.
Synthesis of homopropargyl alcohols via insertion of allenyl carbenoids into acyclic organozirconium bonds
Tetrahedron Letters, 53, (9), . (doi:10.1016/j.tetlet.2011.12.081).
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Insertion of allenylcarbenoids (3-tosyloxy-1-lithioalk-1-ynes) into organozirconium complexes gave allenyl-zirconocenes via a 1,2-zirconate rearrangement. Trapping of the allenyl-zirconium species with aldehydes and ketones gave, after hydrolysis, a series of homopropargylalcohols. Enantioenriched products were prepared by insertion of the lithium carbenoid derived from (S)-but-3-yn-2-yl 4-toluenesulfonate into alkyl- and alkenyl-chlorozirconocenes.
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