430461-41-9

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 430461-07-7 diethyl 3-(1-formylpropyl)glutarate 
• 457622-92-3 (3R,7R,8S,8aR)-7-[2-(ethoxycarbonyl)-1,3-dithiolan-2-yl]-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 66757-48-0 methyl 4-formylhexanoate 
• 817574-26-8 (3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-6-(phenylsulfinyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 457622-91-2 (3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine 
• 194149-76-3 (3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 

Downstream Products

• 457622-95-6 (R)-2-[(3S,4S)-3-Ethyl-4-(2-hydroxy-ethyl)-piperidin-1-yl]-2-phenyl-ethanol 
• 457622-93-4 ethyl (3S,4R)-3-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]piperidine-4-acetate 

Relevant academic research and scientific papers

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.

Conjugate additions to phenylglycinol-derived unsaturated δ-lactams. Enantioselective synthesis of uleine alkaloids

The stereochemical outcome of the conjugate addition of a variety of stabilized nucleophiles (2-indoleacetic enolates and sulfur-stabilized anions) to the phenylglycinol-derived unsaturated lactams trans-2, cis-2, and its 8-ethyl-substituted analogue 10 i

Stereodivergent synthesis of enantiopure cis- and trans-3-ethyl-4-piperidineacetates

(Matrix presented) Starting from a common chiral bicyclic lactam 11, enantiopure trans-or Cis-3-ethyl-4-piperidineacetate derivatives are obtained by conjugate addition of an enolate or a cuprate to the unsaturated lactams 12 or 18, respectively.

Dynamic kinetic resolution and desymmetrization of enantiotopic groups by cyclodehydration of racemic or prochiral δ-oxoesters with (R)-phenylglycinol: Enantioselective synthesis of piperidines

Enantiotopic ester groups are desymmetrized in the cyclodehydration of prochiral δ-oxodiesters with (R)-phenylglycinol. This reaction can be extended to racemic δ-oxodiesters, which undergo a tandem dynamic kinetic resolution-diastereoselective differentiation process (see scheme). The resulting bicyclic lactams can be used in the preparation of a variety of synthetically and pharmacologically interesting enantiopure piperidine derivatives.