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

Pancholi, Alpa K.; Geden, Joanna V.; Clarkson, Guy J.; Shipman, Michael

doi:10.1021/acs.joc.6b01284.s002

jo6b01284_si_002.pdf (9.73 MB)

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

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.