213685-91-7

Upstream product

• 131543-46-9 Glyoxal 
• 194796-70-8 (2R)-2-phenyl-2-(6-trimethylsilanylhex-4-enylamino)ethanol 
• 97997-96-1 (Z)-6-(trimethylsilyl)hex-4-enyl methanesulfonate 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 213685-94-0 (2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester 
• 213685-93-9 (4R,9S,9aS)-4-phenyl-9-vinyloctahydropyrido[2,1-c][1,4]oxazin-1-one 
• 213685-92-8 (4R,9S,9aS)-4-phenyl-9-vinyloctahydropyrido[2,1-c][1,4]oxazin-1-ol 

Relevant academic research and scientific papers

The tetrahydrooxazinone way to enantiopure α-amino acids: Synthesis of cis and trans 3-vinyl pipecolic acids via an intramolecular reaction between an iminium ion and an allylsilane moieties

Reaction of glyoxal with a derivative of (R)-phenylglycinol having an allylsilane side-chain afforded a transient iminium ion. Intramolecular reaction of the iminium ion and the allylsilane moieties occurred in a totally stereoselective way. Straightforward transformations ultimately led to enantiopure either cis or trans 3-vinyl pipecolic acid methyl ester. The stereochemical course of this reaction was rationalized via AMI calculations.