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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
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
0040-4039
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
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), 1112-1115. (doi:10.1016/j.tetlet.2011.12.081).

Record type: Article

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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More information

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
ORCID for Richard J. Whitby: ORCID iD orcid.org/0000-0002-9891-5502

Catalogue record

Date deposited: 24 Apr 2012 09:18
Last modified: 15 Mar 2024 02:34

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Contributors

Author: Jozef Stec
Author: Alan R. Henderson

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