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

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

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 carbon...

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Veröffentlicht in:Journal of organic chemistry 2016-09, Vol.81 (17), p.7984-7992
Hauptverfasser: Pancholi, Alpa K, Geden, Joanna V, Clarkson, Guy J, Shipman, Michael
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01284