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 Shipman2-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.