488785-29-1

Upstream product

• 1186384-46-2 N-((R)-2-((S)-2-hydroxy-1-phenylethoxy)-2-phenylethyl)-4-methylbenzenesulfonamide 
• 1346694-77-6 C₂₃H₂₃NO₄S 
• 70-55-3 toluene-4-sulfonamide 
• 70-11-1 α-bromoacetophenone 
• 80884-48-6 N,N-diphenacyl-p-toluenesulfonamide 
• 884866-01-7 1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 
• 2425-28-7 2-Bromo-1-phenylethanol 
• 57308-70-0 2-iodo-1-phenylethan-1-ol 
• 40434-87-5 toluene-4-sulfonic acid 2-hydroxy-2-phenylethyl ester 
• 821775-66-0 N-((S)-2-Hydroxy-2-phenyl-ethyl)-N-((R)-2-hydroxy-2-phenyl-ethyl)-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2 H-1,4-oxazines

Herein, we report a Rh(II)-catalyzed reaction between 1-tosyl-1,2,3-triazoles and halohydrins to provide 2,6-substituted 3,4-dihydro-2H-1,4-oxazines under basic conditions. The reaction is proposed to undergo a rhodium carbenoid 1,3-insertion into O-H followed by an annulation. The scope includes phenyl or alkenyl C4-substituted triazoles and a range of halohydrins using catalytic Rh2Oct4 and K2CO3. A synthesis of the antimicrobial natural product (±)-chelonin C is also reported using this novel methodology.

Stereoselective synthesis of cis-2,6-disubstituted morpholines and 1,4-oxathianes by intramolecular reductive etherification of 1,5-diketones

A simple and efficient, Lewis acid catalysed reductive etherification strategy for the stereoselective synthesis of cis-2,6- disubstituted morpholines and 1,4-oxathianes starting from readily available 1,5-diketones has been developed. The strategy is used in the total synthesis of morpholine-based natural products (±)-chelonin A and formal total synthesis of (±)-chelonin C.

Stereoselective synthesis of c-substituted morpholine derivatives using reductive etherification reaction: Total synthesis of chelonin C

A general strategy is developed for the stereoselective synthesis of C-substituted morpholine derivatives using intramolecular reductive etherification reaction. The method is extended to the first stereoselective total synthesis of (±)-chelonin C.

Enantioselective syntheses of morpholines and their homologues via S N2-type ring opening of aziridines and azetidines with haloalcohols

(Chemical Equation Presented) A highly regio- and stereoselective strategy for the syntheses in high yield and enantioselectivity of a variety of substituted nonracemic morpholines and their homologues is described. The reaction proceeds via an SN2-type ring opening of activated aziridines and azetidines by suitable halogenated alcohols in the presence of Lewis acid followed by base-mediated intramolecular ring closure of the resulting haloalkoxy amine.

Synthesis of 2,6-disubstituted morpholines through regioselective oxiranes ring opening by tosylamide under PTC conditions

Symmetric and non-symmetric 2,6-disubstituted morpholines were synthesized through regioselective nucleophilic ring opening of oxiranes with tosylamide under solid-liquid phase transfer catalysis (SL-PTC) conditions followed by cyclization of the tosylami