21823-74-5

Upstream product

• 845753-23-3 [2-oxo-5-(3-trimethylsilanyl-propenyl)-pyrrolidin-1-yl]-thioacetic acid S-ethyl ester 
• 56783-28-9 (2S*,3S*)-2,3-dimethyl hexahydropyrrolo[1,2-b][1,2]oxazole-2,3-dicarboxylate 
• 845753-19-7 [2-Oxo-5-((E)-3-trimethylsilanyl-propenyl)-pyrrolidin-1-yl]-acetic acid methyl ester 
• 845753-11-9 N-carbomethoxyamino-5-[3-(trimethylsilyl)-1-propenyl]-2-pyrrolidinone 
• 845753-21-1 [2-Oxo-5-((E)-3-trimethylsilanyl-propenyl)-pyrrolidin-1-yl]-acetic acid 
• 845753-15-3 Methyl-[2-oxo-5-((E)-3-trimethylsilanyl-propenyl)-pyrrolidin-1-yl]-carbamic acid methyl ester 
• 845753-24-4 [2-Oxo-5-((E)-3-trimethylsilanyl-propenyl)-pyrrolidin-1-yl]-acetaldehyde 
• 845753-17-5 5-[3-(trimethylsilyl)-1-propenyl]-2-pyrrolidinone 

Relevant academic research and scientific papers

Synthesis of the necine bases (±)-macronecine and (±)-supinidine via an aza-ene reaction and allylsilane induced ring closure

An aza-ene reaction has been used for the first time for the synthesis of two 5-membered lactam-hydrazides, each with a built-in allylsilane terminator for further elaboration. One of the lactam-hydrazides was transformed via an allylsilane-hydrazonium io

Cascade oxime formation, cyclization to a nitrone, and intermolecular dipolar cycloaddition

Simple haloaldehydes, including enolisable aldehydes, were found to be suitable for the formation of cyclic products by cascade (domino) condensation, cyclisation, dipolar cycloaddition chemistry. This multi-component reaction approach to heterocyclic compounds was explored by using hydroxylamine, a selection of aldehydes, and a selection of activated dipolarophiles. Initial condensation gives intermediate oximes that undergo cyclisation with displacement of halide to give intermediate nitrones; these nitrones undergo in situ intermolecular dipolar cycloaddition reactions to give isoxazolidines. The cycloadducts from using dimethyl fumarate were treated with zinc/acetic acid to give lactam products and this provides an easy way to prepare pyrrolizinones, indolizinones, and pyrrolo[2,1-a]isoquinolinones. The chemistry is illustrated with a very short synthesis of the pyrrolizidine alkaloid macronecine and a formal synthesis of petasinecine.

Extremely high regio- and stereoselective C-C bond formation of substituted γ-hydroxylactams: synthesis of macronecines based on their structural duality

With a view to develop a new synthetic entry for the necine bases, treatment of functionalized γ-hydroxylactams was found to undergo quite high regio- and diastereoselective carbon-carbon bond formation reactions, affording the corresponding structurally