Synthesis 2008(17): 2747-2763  
DOI: 10.1055/s-2008-1067226
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Synthesis of 1-Lithiated Glycals and 1-Tributylstannyl Glycals from 1-Phenylsulfinyl Glycals via Sulfoxide-Lithium Ligand Exchange

Krzysztof Jarowicki, Colin Kilner, Philip J. Kocienski*, Zofia Komsta, Jacqueline E. Milne, Anna Wojtasiewicz, Victoria Coombs
Institute of Process Research and Development, School of Chemistry, Leeds University, Leeds, LS2 9JT, UK
e-Mail: p.j.kocienski@leeds.ac.uk;
Further Information

Publication History

Received 5 May 2008
Publication Date:
13 August 2008 (online)

Abstract

1-Lithiated glycals generated by reaction of 1-phenylsulfinyl glycals with either t-BuLi or PhLi are transformed to 1-tributylstannyl glycals on reaction with tributyltin chloride.

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29

The Bu3SnMgBr was prepared by transmetallation of Bu3SnLi with MgBr2. The Bu3SnLi was prepared, in turn, by the reaction of BuLi with Bu3SnSnBu3 thereby generating 1 equiv of Bu4Sn waste for each equiv of Bu3SnLi.

30

Parker and Su (reference 26) reported a successful metallation of the bis-TBS-protected analogue of 35 using 3 equiv of t-BuLi in THF at -78 ˚C.

40

Crystallographic data for the structures in this paper have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 685328 [( S S )-44], 676297 [(R S)-36], 676296 [(R S)-48], 676300 [(R S)-55], 676298 [(S S)-28], 676301 [(S S)-61], 682926 [(S S)-37]. Copies of these data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk or via www.ccdc.cam.ac.uk/conts/retrieving.html.