919770-45-9

Upstream product

• 1329450-85-2 (R,S)-5-[(R)-phenyl-(tert-butanesulfinylamino)methyl]furan-2(5H)-one 
• 1329451-13-9 (R,S)-5-[(R)-phenyl-(tert-butanesulfinylamino)methyl]furan-2(4H)-one 
• 100-52-7 benzaldehyde 
• 186249-76-3 (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide 
• 33599-84-7 (Z)-5-phenyl-4-pentenoic acid methyl ester 
• 17920-83-1 (4Z)-5-phenylpent-4-enoic acid 
• 1379786-30-7 5-(azido(phenyl)methyl)dihydro-furan-2(3H)-one 
• 1379786-11-4 (R)-5-((R)-bromo(phenyl)methyl)dihydrofuran-2(3H)-one 
• 919770-44-8 (-)-5-[[(2-methoxyphenyl)amino](phenyl)methyl]dihydrofuran-2-one 

Relevant academic research and scientific papers

Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst

A facile, highly regio- and enantioselective amino-thiocarbamate-catalyzed bromolactonization of cis-1,2-disubstituted olefinic acids has been developed. The use of the enantio-enriched lactones in the synthesis of chiral synthetic intermediates is also demonstrated. 2012

Asymmetric vinylogous Mannich reactions: A versatile approach to functionalized heterocycles

Asymmetric vinylogous Mannich reaction (VMR) of 2-(tert- butyldimethylsilyloxy)furan (TBSOF, 1) with (RS)- or (S S)-t-BS-imines (3) furnished 5-aminoalkylbutenolides 7a-k in 75-87% yields with anti/syn ratios ranging from 75:25 to 97:3. Butenolides 7a-f,k were readily converted into substituted lactones 8 and 5 and 6-substituted 5-hydroxypiperidin-2-ones 11a-g, which are, in turn, key intermediates for the synthesis of many bioactive compounds.

A highly efficient and practical method for catalytic Asymmetric Vinylogous Mannich (AVM) reactions

(Chemical Equation Presented) Very selective but very easy: These are two of the attributes of the asymmetric vinylogous Mannich reactions presented herein. These reactions can be run on a gram scale and in undistilled THF and air (see scheme; TMS = SiMe3). All that is needed is commercially available AgOAc, a readily available amino acid derived phosphine, and a commercially available or easily prepared (one step) siloxyfuran.