792908-95-3

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 1041464-25-8 methyl (Z)-1-phenylprop-1-enylcarbamate 
• 942602-56-4 N-((p-chloro)-benzenesulfonyl)-(Z)-1-phenylprop-1-en-1-amine 
• 942602-54-2 N-((p-methyl)-benzenesulfonyl)-(Z)-1-phenylprop-1-en-1-amine 
• 942602-53-1 N-((p-methoxy)-benzenesulfonyl)-(Z)-1-phenylprop-1-en-1-amine 
• 942602-51-9 N-(benzenesulfonyl)-(Z)-1-phenylprop-1-en-1-amine 

Downstream Products

• 792909-10-5 (3S,4S,5R)-3-hydroxy-4-methyl-5-phenyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Iron- and bismuth-catalyzed asymmetric mukaiyama aldol reactions in aqueous media

We have developed asymmetric Mukaiyama aldol reactions of silicon enolates with aldehydes catalyzed by chiral FeII and BiIII complexes. Although previous reactions often required relatively harsh conditions, such as strictly anhydrous conditions, very low temperatures (-78 °C), etc., the reactions reported herein proceeded in the presence of water at 0 °C. To find appropriate chiral water-compatible Lewis acids for the Mukaiyama aldol reaction, many Lewis acids were screened in combination with chiral bipyridine L1, which had previously been found to be a suitable chiral ligand in aqueous media. Three types of chiral catalysts that consisted of a FeII or BiIII metal salt, a chiral ligand (L1), and an additive have been discovered and a wide variety of substrates (silicon enolates and aldehydes) reacted to afford the desired aldol products in high yields with high diastereo- and enantioselectivities through an appropriate selection of one of the three catalytic systems. Mechanistic studies elucidated the coordination environments around the FeII and BiIII centers and the effect of additives on the chiral catalysis. Notably, both Bronsted acids and bases worked as efficient additives in the Fe II-catalyzed reactions. The assumed catalytic cycle and transition states indicated important roles of water in these efficient asymmetric Mukaiyama aldol reactions in aqueous media with the broadly applicable and versatile catalytic systems. Copyright

Highly enantioselective aza-ene-type reaction catalyzed by chiral N,N′-dioxide-nickel(ii) complex

An efficient catalytic enantioselective aza-ene-type reaction of glyoxal derivatives with enamides and enecarbamates has been realized using a nickel(ii)-N,N′-dioxide complex as the catalyst.

Enantioselective activation of aldehydes by chiral phosphoric acid catalysts in an aza-ene-type reaction between glyoxylate and enecarbamate

(Chemical Equation Presented) Double interaction doesit: Highly enantio- and diastereoselective aza-ene-type reaction of glyoxylate with an enecarbamate is accomplished by using a binol-derived phosphoric acid catalyst (see scheme). DFT computational analysis revealed that two hydrogen bonds formed between the catalyst and the aldehyde are critical for the high enantioselectivity.

Enesulfonamides as nucleophiles in catalytic asymmetric reactions

(Chemical Equation Presented) A biased copper-coin toss: Highly diastereo- and enantioselective copper-catalyzed addition reactions of enesulfonamides to α-keto aldehydes and azodicarboxylates have been developed. Low loadings of the chiral copper catalys

Highly diastereo- and enantioselective reactions of enecarbamates with an aldehyde

Catalytic asymmetric addition reactions of enecarbamates with ethyl glyoxylate have been developed using CuClO4·4CH3CN and a diimine ligand as the catalyst. Highly diastereo- and enantioselective addition reactions of α-mono-substitu

Highly diastereo- and enantioselective reactions of enecarbamates with ethyl glyoxylate to give optically active syn and anti α-alkyl-β- hydroxy imines and ketones

The remarkably selective addition of enecarbamates 2 to ethyl glyoxylate (1) in the presence of a copper-dilmine catalyst (0.1 mol%) gives the corresponding imines 3 in high yields with excellent enantioselectivities. A concerted aza-enetype reaction mech