124306-11-2

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 5908-41-8 benzoyltrimethylsilane 
• 19093-37-9 allyl phenyl sulfoxide 
• 495-41-0 1-phenylbut-2-en-1-one 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 77987-25-8 (E)-5-Ethoxy-1-phenyl-hex-2-en-1-one 
• 77987-30-5 2-(1-Ethoxy-ethyl)-1-phenyl-but-3-en-1-one 
• 73311-68-9 1-Phenyl-2-phenylsulfanylmethyl-but-3-en-1-one 
• 73311-69-0 (E)-1-Phenyl-5-phenylsulfanyl-pent-2-en-1-one 
• 73311-70-3 1-Phenyl-3-phenylsulfanyl-2-vinyl-hexan-1-one 
• 73311-71-4 (E)-1-Phenyl-5-phenylsulfanyl-oct-2-en-1-one 
• 147032-71-1 1-phenyl-hept-2-ene-1,6-dione 
• 85920-98-5 (E)-6-Oxo-6-phenyl-2-phenylsulfanyl-hex-4-enoic acid methyl ester 
• 77987-24-7 (E)-5-methoxy-1-phenylpent-2-en-1-one 
• 77987-29-2 2-Methoxymethyl-1-phenyl-but-3-en-1-one 
• 77987-28-1 (E)-5,5-Dimethoxy-1-phenyl-pent-2-en-1-one 
• 1192712-77-8 2-((2S,4R,6R)-4-hydroxy-6-phenyltetrahydro-2H-pyran-2-yl)-1-phenylethan-1-one 

Relevant academic research and scientific papers

Asymmetric synthesis of rauhut-currier type products by a regioselective mukaiyama reaction under bifunctional catalysis

The reactivity and the regioselective functional-ization of silyl-diene enol ethers under a Afunctional organocatalyst provokes a dramatic change in the regioselectiv-ity, from the 1, 5- to the 1, 3-functionalization. This variation makes possible the 1, 3-addition of silyl-dienol ethers to nitroalkenes, giving access to the synthesis of tri- and tetrasubstituted double bonds in Rauhut-Currier type products. The process takes place under smooth conditions, nonanionic conditions, and with a high enantiomeric excess. A rational mechanistic pathway is presented based on DFT and mechanistic experiments.

Total synthesis of (+)-diospongin A

Enantioselective total synthesis of 2,4,6-trisubstituted pyran natural product diospongin A is accomplished from benzaldehyde in 5 steps. Key reaction in the synthesis is the addition of a silyl enol ether derived from vinylogous aryl methyl ketone to chiral β-alkoxy aldehyde and subsequent oxa-Michael addition.

Asymmetric vinylogous Mukaiyama aldol reaction of isatins under bifunctional organocatalysis: Enantioselective synthesis of substituted 3-hydroxy-2-oxindoles

A highly enantioselective organocatalytic vinylogous Mukaiyama aldol reaction of silyloxy dienes and isatins under bifunctional organocatalysis is presented. Substituted 3-hydroxy-2-oxindoles are synthesised in good yields and enantioselectivities. These

A General Asymmetric Formal Synthesis of Aza-Baylis–Hillman Type Products under Bifunctional Catalysis

A new organocatalytic strategy for the synthesis of enantioenriched aza-Baylis–Hillman type products via a frustrated vinylogous reaction is presented. This process proceeds under mild conditions with good yields, completed Z/E selectivity and excellent e

Reaction of acylsilanes with α-sulfinyl carbanions: Regioselective synthesis of silyl enol ethers

The reaction of acylsilanes with α-sulfinyl carbanions such as α-lithioalkyl sulfoxide is described. The reaction proceeds to give silyl enol ethers preferentially through the initial formation of the α-silyl alkoxide intermediates. In particular, the products derived from enolizable acylsilanes were the regio-defined silyl enol ethers that cannot be obtained by usual enolization of the corresponding unsymmetrical ketones with base.

Lewis base activation of Lewis acids: Catalytic, enantioselective vinylogous aldol addition reactions

(Chemical Equation Presented) The generality of Lewis base catalyzed, Lewis acid mediated, enantioselective vinylogous aldol addition reactions has been investigated. The combination of silicon tetrachloride and chiral phosphoramides is a competent catalyst for highly selective additions of a variety of α,β-unsaturated ketone-, 1,3-diketone-, and α,β- unsaturated amide-derived dienolates to aldehydes. These reactions provided high levels of γ-site selectivity for a variety of substitution patterns on the dienyl unit. Both ketone- and morpholine amide-derived dienol ethers afforded high enantio- and diastereoselectivity in the addition to conjugated aldehydes. Although α,β-unsaturated ketone-derived dienolate did not react with aliphatic aldehydes, α,β-unsaturated amide-derived dienolates underwent addition at reasonable rates affording high yields of vinylogous aldol product. The enantioselectivities achieved with the morpholine derived-dienolate in the addition to aliphatic aldehydes was the highest afforded to date with the silicon tetrachloride-chiral phosphoramide system. Furthermore, the ability to cleanly convert the morpholine amide to a methyl ketone was demonstrated.

A REGIOSPECIFIC SYNTHESIS OF γ-KETO ESTERS: THE ALKYLATION OF O-SILYLATED ENOLATES WITH METHYL α-CHLORO-α-PHENYLTHIOACETATE

Methyl α-chloro-α-phenylthio acetate (2) regiospecifically alkylates O-silylated enolates to form γ-keto esters.