704879-65-2

Upstream product

• 105181-72-4 (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid 

Downstream Products

• 93780-03-1 (S)-2-phenylmethylpent-4-enoic acid 
• 704879-67-4 benzyl N-[(4S,5R)-4-benzyl-3-(3-phenylpropionyl)-1,3-oxazolidin-2-one-5-carbonyl]piperidine-4-carboxylate 
• 704879-66-3 benzyl N-[(4S,5R)-4-benzyl-1,3-oxazolidin-2-one-5-carbonyl]piperidine-4-carboxylate 
• 704879-70-9 1-((4S,5R)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-piperidine-4-carboxylic 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.

A new polymer-supported Evans-type chiral auxiliary derived from α-hydroxy-β-amino acid, phenylnorstatine: Synthesis and application in solid-phase asymmetric alkylation reactions

Based on a new anchoring strategy, a polymer-supported chiral oxazolidinone was prepared starting from (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid (phenylnorstatine, Pns) and Wang resin. Solid-phase asymmetric alkylation on this resin proceeded in high diastereoselectivity comparable to that of conventional solution-phase model experiments. This study suggests that anchoring through the 5-position of oxazolidinone is highly suited to achieving diastereoselective alkylation reactions on solid-support.