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β‐Lactams as Formal Dipoles through Amide‐Bond Activation
Author(s) -
Barbier Vincent,
Marrot Jérôme,
Couty François,
David Olivier R. P.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501342
Subject(s) - chemistry , catalysis , amide , lewis acids and bases , combinatorial chemistry , peptide bond , dipole , computational chemistry , polar , organic chemistry , physics , astronomy , enzyme
Abstract Activation of β‐lactams can be achieved by simple Lewis‐base catalysis to trigger an unprecedented reaction based on the formal dipolar behaviour of a strained amide bond. A new synthetic route for 1,3‐oxazinan‐6‐ones is presented by reaction of β‐lactams with ethylglyoxylate, which after methodological optimizations identified 4‐pyrrolidinopyridine as the catalyst of choice in aprotic polar solvents. Mechanistic details are also discussed in light of the intrinsic limitations identified for this transformation.