203576-40-3

Upstream product

• 16854-32-3 (1S,2S)-(+)-thiomicamine 
• 74-88-4 methyl iodide 
• 203576-39-0 (4S,5S)-4-hydroxymethyl-2-methyl-5-[4-(methylthio)phenyl]-2-oxazoline 

Downstream Products

• 494841-80-4 2-chloro-3-{(E)-[2-(4S,5S)-4-methoxymethyl-5-(4-methylthiophenyl)-4,5-dihydro-1,3-oxazol-2-yl]vinyl}pyridine 
• 203576-41-4 C₁₇H₂₆NO₅PS 
• 464170-04-5 2-(N-benzylisopropylamino)-6-chloro-5-{(E)-[2-(4S,5S)-4-methoxymethyl-5-(4-methylthiophenyl)-4,5-dihydro-1,3-oxazol-2-yl]vinyl}pyridine 

Relevant academic research and scientific papers

Enantioselective addition of methyllithium to a prochiral imine - The substrate in the Pomeranz-Fritsch-Bobbitt synthesis of tetrahydroisoquinoline derivatives mediated by chiral monooxazolines

A series of chiral monooxazoline ligands 7-24 with substituents at C-2 and C-4, differing in electronic and steric properties, has been synthesized from (+)-thiomicamine 6. The effect of the oxazoline structure on the course of addition of methyllithium to imine 1 has been studied. The addition product, amine 3, which is the key intermediate in the Pomeranz-Fritsch-Bobbitt synthesis of tetrahydroisoquinoline derivatives, has been obtained in high yield (92%) and with up to 76% ee.

Asymmetric conjugate addition reaction

This invention relates to a key intermediate in the synthesis of an endothelin antagonist the synthesis of this key intermediate via an asymmetric conjugate addition reaction.