917977-23-2

Upstream product

• 65266-23-1 methyl 4-formylhept-6-enoate 
• 56613-80-0 D-2-phenylglycinol 
• 864967-32-8 (3R,8R,8aR)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 

Downstream Products

• 1107664-89-0 (5S,6R)-5,6-diallyl-1-[(1R)-2-hydroxy-1-phenylethyl]-2-piperidone 
• 1107664-90-3 (5S,6S)-5,6-diallyl-1-[(1R)-2-hydroxy-1-phenylethyl]-2-piperidone 

Relevant academic research and scientific papers

Stereocontrolled synthesis of enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones

Starting from the 8-allyl substituted oxazolopiperidone lactam 2b, which is easily accessible from (R)-phenylglycinol and racemic δ-oxoester 1a, two-step sequences involving a stereoselective α-amidoalkylation reaction, either with inversion or retention of configuration, followed by a ring-closing metathesis, provide diastereodivergent routes to enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones.

A general synthetic route to enantiopure cis-fused perhydrocycloalka[c]pyridines from phenylglycinol-derived lactams

A synthetic route to enantiopure piperidines bearing a five-, six-, or seven-membered carbocyclic ring cis-fused on the c side of the heterocycle from a common phenylglycinol-derived δ-lactam is reported. Key steps are (i) a cyclocondensation reaction of

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.

An enantioselective entry to cis-perhydroisoquinolines

(Chemical Equation Presented) An enantioselective route to cis-perhydroisoquinolines, involving a cyclocondensation reaction of (R)-phenylglycinol with a racemic oxoester, a stereoselective conjugate addition to an unsaturated bicyclic lactam, and the clo