113133-50-9

Upstream product

• 6436-91-5 ethyl N-acetyl-N-benzylaminoacetate 
• 16812-43-4 bis(trimethylstannyl)methane 
• 145593-41-5 N-benzyl-2,2,2-trichloro-N-(2-methylallyl)acetamide 
• 52853-55-1 N-benzyl(2-methylallyl)amine 
• 75-36-5 acetyl chloride 

Relevant academic research and scientific papers

α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams

Pyrrolidones are common heterocyclic fragments in various biologically active compounds. Here, a two-step radical-based approach to γ-lactams bearing three to four stereocenters starting from epoxides, N-allylic silylacetamides and TEMPO is reported. The sequence starts with a new tandem nucleophilic substitution/Brook rearrangement/single electron transfer-induced radical oxygenation furnishing orthogonally protected α,γ-dioxygenated N-allylamides with wide scope, mostly good yields, and partly good diastereo- and enantioselectivity for defined combinations of chiral epoxides and chiral amides. This represents a very rare example of an oxidative geminal C–C/C–O difunctionalization next to carbonyl groups. The resulting dioxygenated allylic amides are subsequently subjected to persistent radical effect-based 5-exo-trig radical cyclization reactions providing functionalized pyrrolidones in high yields as diastereomeric mixtures. They converge to 3,4-trans-γ-lactams by base-mediated equilibration, which can be easily further diversified. Stereochemical models for both reaction types were developed.

Synthesis of substituted γ- And δ-lactams based on titanocene(III)-catalysed radical cyclisations of trichloroacetamides

A new procedure for the synthesis of γ- and δ-lactams based on a Cp2TiCl-catalysed cyclisation of trichloroacetamides under mild reaction conditions is reported. Theoretical studies supported the observed regioselectivity in the cyclisations and the mechanism involved in the dehalogenation process.

Trisubstituted (Stannylmethyl)lithium as a Methylene Double Anion Equivalent. Reaction with Esters

Trisubstituted (stannylmethyl)lithium reacts with electrophiles as a methylene double anion equivalent to produce enolates from esters.The reaction mechanism is discussed.