226970-62-3

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 216569-15-2 (5R)-4-Benzyl-5-phenyl[1,3,4]oxadiazinan-2-one 
• 216569-13-0 (2R)-2-(N-Benzylnitrosoamino)-2-phenylethanol 
• 216569-14-1 (2R)-2-(N-Benzylhydrazino)-2-phenylethanol 
• 216569-16-3 (5R)-5-Phenyl[1,3,4]oxadiazinan-2-one 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 

Downstream Products

• 226970-66-7 (2R)-1-(2-Hydroxy-1-phenylethyl)-5-phenyl-1H-pyrazole-3,4-dicarboxylic acid diethyl ester 

Relevant academic research and scientific papers

Diastereoselective cycloadditions of chiral non-racemic azomethine imines

(5R)-5-Phenyl[1,3,4]oxadiazinan-2-one (6) is an easily available building block and acts as a chiral non-racemic precursor for azomethine imines. The ylid can be formed regioselectively with various aldehydes and reacts in an efficient manner with a wide range of dipolarophiles. The regio- and diastereoselectivity of the cycloadditions have been fully investigated and can lead, in the best cases, to the creation of three contiguous asymmetric centers in a single step, with complete control of relative and absolute configurations.

Asymmetric 1, 3-dipolar cycloadditions of a chiral non-racemic azomethine imineo

Chiral non racemic carbazate 1, derived from (R)-(-)-phenylglycinol, reacts regioselectively with benzaldehyde or its dimethylacetal to give an azomethine imine. The facial, endo/exo and regio selectivities of 1,3- dipolar cycloadditions of this reactive species with various dipolarophiles have been studied and are described in this paper. In the best cases, up to three contiguous asymmetric centers could be generated simultaneously, in a complete enantio- and diastereoselective fashion.