[reaction: see text] Enantiopure alpha-alkoxy beta-lactam acetaldehydes were prepared via the thiazole-based one-carbon homologation. The 1,3-dipolar cycloaddition reaction involving alpha-alkoxy beta-lactam acetaldehyde-derived azomethine ylides gave with excellent diastereoselectivity highly functionalized 2-azetidinone-tethered prolines, which were directly used for the first preparation of azabicyclo[4.3.0]nonane (indolizidinone) amino esters from beta-lactams.
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Alcaide et al. (2005) studied this question.
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