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Asymmetric Synthesis of 2‑Substituted Azetidin-3-ones via Metalated SAMP/RAMP Hydrazones

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journal contribution
posted on 2016-07-22, 00:00 authored by Alpa K. Pancholi, Joanna V. Geden, Guy J. Clarkson, Michael Shipman
2-Substituted azetidin-3-ones can be prepared in good yields and enantioselectivities (up to 85% ee) by a one-pot procedure involving the metalation of the SAMP/RAMP hydrazones of N-Boc-azetidin-3-one, reaction with a wide range of electrophiles, including alkyl, allyl, and benzyl halides and carbonyl compounds, followed by hydrolysis using oxalic acid.

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