Synthesis of homopropargyl alcohols via insertion of allenyl carbenoids into acyclic organozirconium bonds


Stec, Jozef, Henderson, Alan R. and Whitby, Richard J. (2012) Synthesis of homopropargyl alcohols via insertion of allenyl carbenoids into acyclic organozirconium bonds. Tetrahedron Letters, 53, (9), 1112-1115. (doi:10.1016/j.tetlet.2011.12.081).

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Description/Abstract

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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/j.tetlet.2011.12.081
ISSNs: 0040-4039 (print)
1873-3581 (electronic)
Keywords: homopropargylalcohol, metallate rearrangement, organozirconium chemistry, asymmetric synthesis, carbenoids
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural and Environmental Sciences > Chemistry > Organic Chemistry: Synthesis, Catalysis and Flow
ePrint ID: 337313
Date :
Date Event
29 February 2012Published
Date Deposited: 24 Apr 2012 09:18
Last Modified: 31 Mar 2016 14:26
URI: http://eprints.soton.ac.uk/id/eprint/337313

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