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Asymmetric synthesis of β-lactams by [2+2] cycloaddition using 1,4:3,6-dianhydro-d-glucitol (isosorbide) derived chiral pools |
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| Authors: | AL Shaikh Md Abrar Shaikh ARAS Deshmukh |
| Institution: | a Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune-411 008, Maharashtra, India b Centre for Materials Characterization, National Chemical Laboratory, Pune-411 008, Maharashtra, India c Emcure Pharmaceuticals Limited, API R&D, ARC-H, P-2, I.T.-B.T. Park, Phase-II, M.I.D.C., Hinjwadi, Pune-411 057, Maharashtra, India |
| Abstract: | Highly diastereoselective synthesis of cis-β-lactams via 2+2] cycloaddition reactions of imines derived from a chiral bicyclic aldehyde and ketenes is described. The chiral bicyclic aldehyde as well as chiral acids were prepared from commercially available inexpensive isosorbide. The cycloaddition reaction was found to be highly diastereoselective; in some cases giving a single diastereomer of cis-azetidin-2-one in very good yields. A moderate diastereoselectivity was observed with chiral ketenes derived from isosorbide. |
| Keywords: | Asymmetric synthesis Staudinger reaction Ketenes Imines Azetidinones |
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