N-(Alkylsulfamoyl)aldimines: easily deprotected precursors for diarylmethylamine synthesis |
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| Authors: | Rosemary H. Crampton Martin Fox Simon Woodward |
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| Affiliation: | 1. School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom;2. Chirotech Technology Centre, Dr. Reddy’s Laboratories EU Ltd, Unit 410 Cambridge Science Park, Milton Road, Cambridge CB4 0PE, United Kingdom |
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| Abstract: | The sequential reaction of chlorosulfonyl isocyanate with t-BuOH, t-BuNH2 and TFA allows formation of H2NSO2NHBut. Condensation of the latter with Ar1CHO in the presence of Ti(OEt)4 provides the activated imines Ar1CH NSO2NHBut (59–89%). Commercially available boronic acids add to these imines with good stereoselectivity (76–98% ee) using readily available diene ligands. Simple deprotection with 5% w/w water in pyridine affords free Ar1CHNH2Ar2. |
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