205526-55-2

Upstream product

• 205526-54-1 (2R,9R)-2,9-diphenyl-1-aza-4-oxabicyclo[4.3.0]nonane 
• 439084-69-2 (3R,8aR)-5-oxo-3,8a-diphenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 56613-80-0 D-2-phenylglycinol 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 204845-22-7 (R)-N-2,4,6-trimethoxybenzylphenylglycinol 
• 205526-52-9 (2R,4R)-2-(3-[1,3]Dioxolan-2-yl-propyl)-4-phenyl-3-(2,4,6-trimethoxy-benzyl)-oxazolidine 
• 205526-53-0 (1R,1'R)-2-[N-(2,4,6-trimethoxybenzyl)-N-2'-hydroxy-1'-phenylethylamino]-5,5-ethylenedioxy-1-phenylpentane 

Downstream Products

• 3466-80-6 (R)-(+)-6-phenylpiperidine 

Relevant academic research and scientific papers

Access to optically pure nitrogen heterocycles based on hydrozirconation of unsaturated secondary amines

Optically active N-heterocycles with four-, five-, or six-membered rings can be prepared from unsaturated secondary amines, by using a one-pot hydrozirconation/iodination sequence as the key step. The presented method allows the preparation of 2-substituted pyrrolidines enantiomeric to those previously obtained from N-allyloxazolidines. The two approaches use the same reagents (allyl bromide and aldehydes) and the same (R)-2-phenyl-glycinol as the chiral inductor. Georg Thieme Verlag Stuttgart.

Dynamic kinetic resolution and desymmetrization processes: A straightforward methodology for the enantioselective synthesis of piperidines

A straightforward procedure for the synthesis of enantiopure polysubstituted piperidines is reported. It involves the direct generation of chiral non-racemic oxazolo[3,2-a]piperidone lactams that already incorporate carbon substituents on the heterocyclic ring and the subsequent removal of the chiral auxiliary. The key step is a cyclocondensation reaction of (R)-phenylglycinol or other amino alcohols with racemic or prochiral δ-oxo (di)acid derivatives in highly stereoselective processes involving dynamic kinetic resolution and/or desymmetrization of diastereotopic or enantiotopic ester groups.

Enantioselective synthesis of 2-arylpiperidines from chiral lactams. A concise synthesis of (-)-anabasine

Cyclodehydration of achiral or racemic aryl-δ-oxoacids with (R)-phenylglycinol stereoselectively affords chiral non-racemic bicyclic lactams, from which the enantiodivergent synthesis of (R)- and (S)-2-phenylpiperidine, the diastereodivergent synthesis of cis- and trans-3-ethyl-2-phenylpiperidine, and the enantioselective synthesis of the piperidine alkaloid (-)-anabasine is reported.

Facile diastereoselective reactions of chiral 1,3-oxazolidines with grignard reagents; asymmetric syntheses of 2-substituted and 2,6-disubstituted piperidines

(S)- and (R)-2-Phenylpiperidines, (S)- and (R)-2-methylpiperidines, meso- and (2R, 6R)-2,6-diphenylpiperidines, and meso- and (25, 65)-2,6-dimethylpiperidines were synthesized asymmetrically starting from the diastereoselective addition of Grignard reagents to chiral 1,3-oxazolidines, converting of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives as pivotal intermediates.