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Synlett 1995; 1995(2): 155-156
DOI: 10.1055/s-1995-4891
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Selective Monoacylation of 2,2’-Binaphthol as a Route to New Monothiobinaphthol-based Copper Catalysts for Conjugate Addition

Jason Green, Simon Woodward*
  • *School of Chemistry, University of Hull, Cottingham Road, Kingston-Upon-Hull HU6 7RX, UK
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Publication History

Publication Date:
31 December 2000 (online)

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Simple procedures allow selective monoacylation of 2,2’-binaphthol and transformation of one OH to an SH in three steps on a large scale without chromatography. 2,2’-Monothiobinaphthol forms an effective catalyst for conjugate addition of BunLi to 2-cyclohexen-1-one in the presence of [Cu(MeCN)4]BF4.

binaphthol - stannylene acetal - Newman-Kwart rearrangement - conjugate addition - copper catalysed