Helvetica Chimica Acta p. 155 - 161 (1985)
Update date:2022-08-10
Topics:
Weber, Theodor
Seebach, Dieter
O-Acetyl-4-hydroxyproline (1b) is condensed with pivalaldehyde to give a single stereoisomer of the 2-(tert-butyl)-4-oxo-3-oxa-1-azabicyclo<3.3.0>oct-7-yl acetate (3).This is converted to the enolates 4 or 5, reactions of which with alkyl halides, aldehydes, and acetone (-->6,9,10,11) are diastereoselective (lk-1,3-induction).Cleavage of the corresponding products furnishes the enantiomerically pure 2-deuterio-, 2-methyl-, 2-allyl-, and 2-benzyl-substituted 4-hydroxyprolines 2a-2d.
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