677729-70-3

Upstream product

• 677729-68-9 (E)-1-morpholin-4-yl-5-phenyl-pent-2-en-1-one 
• 24271-22-5 5-phenyl-2(E)-pentenoic acid 
• 485809-19-6 5-phenyl-2-pentenoic acid chloride 

Downstream Products

• 695176-74-0 4-[(2R,3S,5R,7S)-2,3-epoxy-9-phenyl-5,7-bis(triethylsilyloxy)nonyl]morpholine 
• 695177-15-2 4-[(2E,5R,7S)-1-oxo-9-phenyl-5,7-bis(triethylsilyloxy)-2-nonenyl]morpholine 
• 695177-13-0 ethyl (3S,5S)-7-phenyl-3,5-bis(triethylsilyloxy)heptanoate 
• 695176-65-9 (3S,5S)-7-Phenyl-3,5-bis-triethylsilanyloxy-heptanal 
• 695177-14-1 4-[(2E,5R,7S)-5,7-bis(methoxymethyloxy)-1-oxo-9-phenyl-2-nonenyl]morpholine 
• 677729-72-5 4-[(2R,3S,5R,7S)-2,3-epoxy-5,7-isopropylidenedioxy-1-oxo-9-phenylnonyl]morpholine 
• 695176-84-2 ethyl (5S,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate 
• 695176-82-0 ethyl (4R,5S,7R,9S)-4,5-epoxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate 
• 695177-12-9 (3S,5S)-3,5-Bis-methoxymethoxy-7-phenyl-heptanoic acid ethyl ester 
• 502690-24-6 ethyl (4R,5S)-4,5-epoxy-3-oxo-5-phenethylpentanoate 

Relevant academic research and scientific papers

Dynamic ligand exchange of the lanthanide complex leading to structural and functional transformation: One-pot sequential catalytic asymmetric epoxidation-regioselective epoxide-opening process

The characteristic property of the lanthanide complex, which easily undergoes a dynamic ligand exchange and alters its structure and function in situ, is described. After the completion of the catalytic asymmetric epoxidation of various α,β-unsaturated amides 2 in the presence of the Sm-(S)-BINOL-Ph3-As=O (1:1:1) complex 1 (2-10 mol %), the addition of Me3SiN3 directly to the reaction mixture led to smooth epoxide-opening at room temperature, affording the corresponding anti-β-azido-α-hydroxyamide 4 in excellent overall yield (up to 99%) with complete regioselectivity and excellent enantiomeric excess (up to >99%). The key to the success of the sequential process was the in situ generation of the highly reactive samarium azide complex through dynamic ligand exchange. In situ IR spectroscopy and other experiments provided strong evidence that the samarium azide complex was generated. In addition, the relatively high Lewis basicity of the amide moiety had a key role in the high reactivity of both the epoxidation and the epoxide-opening reactions. Examinations of other nucleophiles such as sulfur or carbon nucleophiles as well as transformations of epoxide-opened products are also described.

Strategy for Enantio- and Diastereoselective Syntheses of All Possible Stereoisomers of 1,3-Polyol Arrays Based on a Highly Catalyst-Controlled Epoxidation of α,β-Unsaturated Morpholinyl Amides: Application to Natural Product Synthesis

We describe a new strategy for enantio- and diastereoselective syntheses of all possible stereoisomers of 1,3-polyol arrays. This strategy relies on a highly catalyst-controlled epoxidation of α,β-unsaturated morpholinyl amides promoted by the Sm-BINOL-Ph