762269-35-2

Upstream product

• 762269-31-8 (4-hydroxymethyl-2-phenyl-3-thiophen-2-yl-[1,2]oxazinan-4-yl)-methanol 
• 116-11-0 2-Methoxypropene 
• 6914-71-2 dimethyl 1,1-cyclopropanedicarboxylate 
• 100-65-2 N-Phenylhydroxylamine 
• 848587-08-6 2-phenyl-3-thiophen-2-yl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

Diastereoselective synthesis of pyrrolidines using a nitrone/cyclopropane cycloaddition: Synthesis of the tetracyclic core of nakadomarin A

(Chemical Equation Presented) The synthesis of the tetracyclic core of nakadomarin A is described. The core contains all the heterocycles and the required stereocenters found in the natural product and provides a promising route to the target itself. The strategy utilizes a general, diastereoselective pyrrolidine synthesis that proceeds via a homo 3 + 2 dipolar cycloaddition. The scope of this methodology is also described.

SYNTHESIS OF TETRAHYDRO-1,2-OXAZINES BY THE CYCLOADDITION OF NITRONES WITH CYCLOPROPANES

One aspect of the present invention relates to a method of preparing tetrahydro-1,2- oxazines comprising the step of combining a nitrone and a cyclopropane in the presence of a Lewis acid. Another aspect of the present invention relates to a method of preparing a tetrahydro-1,2-oxazine, comprising the step of combining an aldehyde and a hydroxylamine in the presence of a Lewis acid to generate a nitrone in situ, then admixing a cyclopropane. Another aspect of the present invention relates to converting a tetrahydro-l,2-oxazine to a pyrrolidine comprising the step of admixing a tetrahydro-1,2-oxazine and a reducing agent.