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Relevant academic research and scientific papers

General one-pot reductive gem-bis-alkylation of tertiary lactams/amides: Rapid construction of 1-azaspirocycles and formal total synthesis of (±)-cephalotaxine

Amides are a class of highly stable and readily available compounds. The amide functional group constitutes a class of powerful directing/activating and protecting group for C-C bond formation. Tertiary tert-alkylamine, including 1-azaspirocycle is a key structural feature found in many bioactive natural products and pharmaceuticals. The transformation of amides into tert-alkylamines generally requires several steps. In this paper, we report the full details of the first general method for the direct transformation of tertiary lactams/amides into tert-alkylamines. The method is based on in situ activation of amide with triflic anhydride/2,6-di-tert-butyl-4-methylpyridine (DTBMP), followed by successive addition of two organometallic reagents of the same or different kinds to form two C-C bonds. Both alkyl and functionalized organometallic reagents and enolates can be used as the nucleophiles. The method displayed excellent 1,2- and good 1,3-asymmetric induction. Construction of 1-azaspirocycles from lactams required only two steps or even one-step by direct spiroannelation of lactams. The power of the method was demonstrated by a concise formal total synthesis of racemic cephalotaxine. Four bonds in one pot! Cleavage of two bonds of an amide carbonyl group and replacement by two new C-C bonds can be achieved in one pot under mild conditions by using amide activation with triflic anhydride (Tf2O). A concise formal total synthesis of racemic cephalotaxine has been accomplished by means of this methodology (see scheme; DTBMP=2,6-di-tert-butyl-4-methylpyridine). Copyright

Direct, one-pot sequential reductive alkylation of lactams/amides with grignard and Organolithium reagents through lactam/amide activation

(Figure Presented) Be dazzled by the sequence: The first efficient and general one-pot method for the reductive bisalkylation of lactams/ amides with Grignard and organolithium reagents has been developed (see scheme; DTBMP = 2,6-di-tert-butyl-4methylpyridine, Tf=trifluoromethanesulfonyl).