LiAlH4 reduction of tert-butyl (S)-butyl(1-((2-cycloheptylethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (1) gave imidazolidine 2, while treatment with lithium diisopropylamide furnished the β-elimination product, cinnamamide 3. Both products were fully characterized. Reductive cyclization of N-alkylated-N-Boc-protected amino acid amides with LiAlH4 may be a viable synthetic method for trisubstituted chiral imidazolidines.
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Matevž Schweiger
Luka Ciber
Nejc Petek
Molbank
University of Ljubljana
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Schweiger et al. (Thu,) studied this question.
www.synapsesocial.com/papers/69e320fd40886becb65402fa — DOI: https://doi.org/10.3390/m2166
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