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Asymmetric synthesis of cis-2,4-disubstituted azetidin-3-ones from metal carbene chemistry

2005; Elsevier BV; Volume: 690; Issue: 24-25 Linguagem: Inglês

10.1016/j.jorganchem.2005.07.016

1872-8561

Antonio C. B. Burtoloso, Carlos Roque D. Correia,

Synthesis and Catalytic Reactions

Several chiral cis-2,4-disubstituted azetidin-3-ones were prepared as single diastereoisomers from N-protected amino acids, employing a highly stereoselective copper carbenoid N–H insertion reaction of diazoketones. These azetidin-3-ones were then converted into fully substituted azetidines in a few steps in good to high yields.