Synthesis 2008(17): 2747-2763  
DOI: 10.1055/s-2008-1067226
© 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
Further Information

Publication History

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


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.


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.


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.


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: or via