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Asymmetric synthesis of azetidin-2-ones by [2+2] cycloaddition using chiral imines derived from d-(+)-glucose |
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| Authors: | M ArunS.N Joshi V.G PuranikB.M Bhawal A.R.A.S Deshmukh |
| Affiliation: | a Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India b Division of Physical Chemistry, National Chemical Laboratory, Pune 411 008, India c Emcure Pharmaceuticals Ltd., Emcure House, T-184, M.I.D.C. Bhosari, Pune 411 026, India |
| Abstract: | Asymmetric synthesis of β-lactams by the [2+2] cycloaddition of ketenes with chiral imines derived from d-(+)-glucose was carried out; predominantly cis-β-lactams were formed with very high diastereoselectivity. The stereochemistry at C-3 and C-4 was established as 3S and 4R from the known absolute configuration of the sugar moiety. |
| Keywords: | asymmetric synthesis ketenes imines Staudinger reaction |
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