Synthesis of homopropargyl alcohols via insertion of allenyl carbenoids into acyclic organozirconium bonds
Synthesis of homopropargyl alcohols via insertion of allenyl carbenoids into acyclic organozirconium bonds
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.
homopropargylalcohol, metallate rearrangement, organozirconium chemistry, asymmetric synthesis, carbenoids
1112-1115
Stec, Jozef
c8ef34c5-6d89-453b-a8aa-86d7b54864c4
Henderson, Alan R.
1e96de1a-e70b-43e4-aa4f-456a3a00a6dd
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
29 February 2012
Stec, Jozef
c8ef34c5-6d89-453b-a8aa-86d7b54864c4
Henderson, Alan R.
1e96de1a-e70b-43e4-aa4f-456a3a00a6dd
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
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), .
(doi:10.1016/j.tetlet.2011.12.081).
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.
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Published date: 29 February 2012
Keywords:
homopropargylalcohol, metallate rearrangement, organozirconium chemistry, asymmetric synthesis, carbenoids
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 337313
URI: http://eprints.soton.ac.uk/id/eprint/337313
ISSN: 0040-4039
PURE UUID: 5a2c9b3c-e08a-46f9-ab0a-721409badec5
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Date deposited: 24 Apr 2012 09:18
Last modified: 15 Mar 2024 02:34
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Author:
Jozef Stec
Author:
Alan R. Henderson
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