194796-71-9

Upstream product

• 97997-91-6 (Z)-6-(trimethylsilyl)hex-4-en-1-ol 
• 56613-80-0 D-2-phenylglycinol 
• 131543-46-9 Glyoxal 
• 108-98-5 thiophenol 
• 194796-70-8 (2R)-2-phenyl-2-(6-trimethylsilanylhex-4-enylamino)ethanol 
• 97997-96-1 (Z)-6-(trimethylsilyl)hex-4-enyl methanesulfonate 

Downstream Products

• 194796-72-0 (3R,5R)-5-phenyl-3-phenylsulfanyl-4-(6-trimethylsilanylhex-4-enyl)-2-trimethylsilyloxymorpholine 
• 194796-75-3 (2R,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester 
• 194796-73-1 (4R)-4-phenyl-9-vinyloctahydropyrido[2,1-c][1,4]-1-trimethylsilyloxyoxazine 
• 194796-74-2 (4R,9S,9aR)-4-phenyl-9-vinyloctahydropyrido[2,1-c][1,4]oxazin-1-one 
• 194796-81-1 (4R,9S,9aR)-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.

Asymmetric Synthesis of Unsaturated Pipecolic Acid Derivatives

Two enantiopure pipecolic acid derivatives having an olefinic moiety were synthesized from an intramolecular addition of allyl silanes on an iminium double bond. The iminium moiety was generated via a reaction of chiral β-amino alcohols with glyoxal.