An unexpected Mitsunobu reaction. A direct route to the 2, 5-diazabicyclo [2.2. 1] heptan-3-one skeleton as a γ-lactam mimic of β-lactam antibiotics

PS Hadfield, RHB Galt, NJ Layland…

Index: Hadfield, Peter S.; Galt, Ron H. B.; Sawyer, Yvonne; Layland, Nicola J.; Page, Michael I. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 4 p. 503 - 509

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Abstract

Treatment of anilides of N-protected (2S, 4R)-4-hydroxyproline, eg 1, with thioacetic acid under Mitsunobu conditions gives, unexpectedly, 2, 5-diazabicyclo [2.2. 1] heptan-3-ones, eg 2, the products of intramolecular cyclisation. However, the less acidic N-benzylamides of these proline derivatives, eg 7, are not sufficiently acidic and the hydrazido anion generated in the Mitsunobu reaction displaces the activated hydroxy group in an intermolecular ...