704879-70-9

Upstream product

• 704879-67-4 benzyl N-[(4S,5R)-4-benzyl-3-(3-phenylpropionyl)-1,3-oxazolidin-2-one-5-carbonyl]piperidine-4-carboxylate 
• 704879-65-2 1-((2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-piperidine-4-carboxylic acid benzyl ester 
• 105181-72-4 (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid 
• 62023-65-8 (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 851968-91-7 benzyl N-[(4S,5S)-4-benzyl-3-(3-phenylpropionyl)-1,3-oxazolidin-2-one-5-carbonyl]piperidine-4-carboxylate 
• 851968-89-3 benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate 
• 704879-66-3 benzyl N-[(4S,5R)-4-benzyl-1,3-oxazolidin-2-one-5-carbonyl]piperidine-4-carboxylate 
• 851968-90-6 benzyl N-[(4S,5S)-4-benzyl-1,3-oxazolidin-2-one-5-carbonyl]piperidine-4-carboxylate 

Downstream Products

• 21654-17-1 (R)-2-benzyl-4-ethoxy-4-oxobutanoic acid 

Relevant academic research and scientific papers

Design and synthesis of a new polymer-supported Evans-type oxazolidinone: An efficient chiral auxiliary in the solid-ph ase asymmetric alkylation reactions

Wang resin-supported Evans' chiral auxiliary (23) was designed based on a novel polymer-anchoring strategy, which utilizes the 5-position of the oxazolidinone ring, and its new synthetic route applicable to multi-gram preparation in just a day was developed. Solid-phase Evans' asymmetric alkylation on 23-derived N-acylimide resin and following lithium hydroperoxide-mediated chemoselective hydrolysis afforded the corresponding α-branched carboxylic acids in desired high stereoselectivities (up to 97% ee) and moderate to good overall yield (up to 70%, for 3 steps), which were comparable to those of the conventional solution-phase methods. Furthermore, recovery and recycling of the polymer-supported chiral auxiliary were successfully achieved without decreasing the stereoselectivity of the product. Therefore, this is the first successful example that the solid-phase Evans' asymmetric enolate-alkylation was efficiently performed on the solid-support, and it is concluded that the connection to the solid-support via the 5-position of the oxazolidinone ring is an ideal strategy in the solid-phase Evans' chiral auxiliary.