Alkylierung in der 2‐Stellung von (2S, 4R)‐ 4‐Hydroxyprolin unter Retention
作者： Theodor Weber , Dieter Seebach
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摘要: Alkylation in the 2-Position of (2S, 4R)-4-Hydroxyproline with Retention Configuration O-Acetyl-4-hydroxyproline (1b) is condensed pivalaldehyde to give a single stereoisomer 2-(tert-butyl)-4-oxo-3-oxa-1-azabicyclo[3.3.0]oct-7-yl acetate (3). This converted enolates 4 or 5, reactions which alkyl halides, aldehydes, and acetone (6,9,10,11) are diastereoselective (lk-1,3-induction). Cleavage corresponding products furnishes enantiomerically pure 2-deuterio-, 2-methyl-, 2-allyl-, 2-benzyl-substituted 4-hydroxyprolines 2a–2d.
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