The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage—a method for recycling t-BuSONH2 |
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| Authors: | Varinder K. Aggarwal,Nekane Barbero,Eoghan M. McGarrigle,Greg Mickle,Raquel Navas,José Ramó n Suá rez,Matthew G. Unthank,Muhammad Yar |
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| Affiliation: | School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK |
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| Abstract: | Ellman’s chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH2. |
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| Keywords: | Ellman&rsquo s auxiliary tert-Butylsulfinamide Sulfinimines Deprotection Cleavage Dynamic kinetic resolution |
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