156365-91-2

Upstream product

• 156365-81-0 (2S,4S,5R)-4-methyl-2-(1-oxo-1-phenyl)methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine 
• 762-72-1 allyl-trimethyl-silane 
• 1074-12-0 phenylglyoxal hydrate 
• 492-41-1 (1R,2S)-norephedrine 

Downstream Products

• 110577-94-1 (2R)-1,2-dihydroxy-2-phenylpent-4-ene 

Relevant academic research and scientific papers

N-Boc 2-acyloxazolidines: Useful precursors to enantiopure 1,2-diols via highly diastereoselective nucleophilic additions

N-Boc 2-Acyloxazolidines were synthesized from norephedrine and phenylglycinol. This preparation involves: (i) a transformation or the above β-amino alcohols into N-Boc 2-ethoxycarbonyloxazolidines, (ii) the formation of the corresponding Weinreb amides and, (iii) a reaction between these amides and organometallic reagents. Such diastereomerically pure heterocycles react cleanly with various nucleophilic reagents (Grignard reagents, sodium borohydride and allylsilane) to afford the corresponding alcohols. Treatment of these hydroxyoxazolidines with trifluoro acetic acid, followed by hydrolysis and reduction of the intermediate α-hydroxy aldehydes afforded 1,2-diols. The overall transformation exhibited in most cases a complete diastereoselectivity which can be explained by a chelated model for the nucleophilic addition.

Asymmetric Synthesis of Homochiral 1,2-Diols via N-Boc Oxazolidines

Diastereoisomerically pure N-Boc 2-acyloxazolidines were synthesized from phenylglyoxal and ethyl glyoxylate.Reaction of these heterocycles with Grignard reagents is highly stereoselective.Homochiral 1,2-diols were ultimately obtained after N-deprotection, hydrolysis and reduction of the intermediate α-hydroxy aldehyde.The asymmetric induction can be explained by a chelated model.