A Contribution to the Asymmetric Synthesis of 3‐Amino β‐Lactams: The Diastereoselective [2+2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde‐Derived Imines
作者： Claudio Palomo , Jesus M. Aizpurua , Marta Legido , Antonia Mielgo , Regina Galarza
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摘要: N-[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3-amino-4-alkyl-β-lactams 16 17 in good yields high diastereoselectivities. The mild deprotection bis(trimethylsilyl)methyl- phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate lithium/ammonia or hydrogen/Pd(OH)2 allows preparation a variety β-lactam antibiotic building blocks.
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