112303-67-0

Upstream product

• 999-90-6 S-tert-butyl thioacetate 
• 100-52-7 benzaldehyde 
• 163881-60-5 (2S,3S)-2-Chloro-3-hydroxy-3-phenyl-thiopropionic acid S-tert-butyl ester 
• 175227-32-4 (S)-3-((R)-1-Methyl-3-oxo-propoxy)-3-phenyl-thiopropionic acid S-tert-butyl ester 
• 63584-47-4 (1-tert-butylsulfanyl-vinyloxy)trimethylsilane 
• 175227-22-2 (S)-3-((R)-3-Hydroxy-1-methyl-propoxy)-3-phenyl-thiopropionic acid S-tert-butyl ester 
• 56377-45-8 Chlorthioessigsaeure-S-tert-butylester 
• 53635-52-2 S-tert-butyl 2-bromoethanethioate 
• 175227-31-3 (S)-3-((R)-1-Methyl-3-trimethylsilanyloxy-propoxy)-3-phenyl-thiopropionic acid S-tert-butyl ester 
• 79464-76-9 (2S,4R)-4-methyl-2-phenyl-1,3-dioxane 
• 163881-61-6 (2S,3S)-2-Bromo-3-hydroxy-3-phenyl-thiopropionic acid S-tert-butyl ester 
• 63584-41-8 1-ethylthio-1-(trimethylsiloxy)ethene 

Relevant academic research and scientific papers

Catalytic, enantioselective hetero-Diels-Alder reaction with novel, chiral bis-titanium(IV) catalyst

Our recently designed chiral bis-titanium(IV) catalyst can be successfully utilized for the catalytic enantioselective hetero-Diels-Alder reaction of aldehyde and Danishefsky's diene. The high asymmetric induction is achievable in the case of sterically l

Optimisation, scope and limitations of enantioselective aldol reactions of an S-ketene silyl acetal with aliphatic aldehydes under (R)-BINOL-titanium(IV) catalysis conditions

The Mukaiyama aldol reaction between the functionalised aldehydes 5 and the S-ketene silyl acetal 2 catalysed by 1,1'-binaphthyl-derived chiral titanium(IV) complex 4 afforded the corresponding aldol products 6 in good yields and with good to excellent enantioselectivities. The chemical yield could further be enhanced, without loss of stereoselection, by addition of phenol and/or molecular sieves. The presented aldol reactions with aluminium, boron and ytterbium-BINOL catalysts demonstrate that only low chiral induction can be achieved. Aldol product 6a was converted into an α-lipoic acid precursor 8, thus providing a formal synthesis of this biologically active compound. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Asymmetric Synthesis of Functionalized Secondary Alcohols by Catalytic Ring-Cleavage Reactions of Cyclic Acetals Derived from (R)-1,3-Butanediol

In the presence of a catalytic amount (0.1-0.2 molar amount) of a 2-phenyl-1,3,2-oxazaborolidin-5-one, prepared by the reaction of dichlorophenylborane and N-(trifluoromethylsulfonyl)-L- phenylalanine, and enol silyl ethers ((R2)2C=C-(R3)OTMS; R3 = t-BuS, EtS, EtO, Ph) (1.1-1.5 molar amount), chiral cyclic acetals 6 derived from (R)-1,3-butanediol and aldehydes undergo an efficient ring-cleavage reaction with the inversion of the stereochemistry at the acetal carbon to give the anti isomer of the corresponding products with high stereoselectivity. The reaction is applicable to acetals derived from aromatic, aliphatic, and α,β-unsaturated aldehydes. Not only enol silyl ethers, but also methallyltrimethylsilane and allyltributyltin, can be employed as nucleophiles, leading to the selective formation of the anti isomer of the corresponding allylated ring-cleavage products. Removal of the chiral auxiliary from these ring-cleavage products by a two-step sequence ((i) PCC (ii) Bn2NH2(CF3CO2)) furnishes enantiomerically enriched β-hydroxy carbonyl compounds and homoallyl alcohols. A modest level of kinetic resolution is observed in the ring cleavage of a racemic acetal catalyzed by a phenylboron compound derived from N-mesyl-L-phenylalanine.

A Highly Enantio- and Diastereoselective Aldol Reaction for α-Heterosubstituted Thioacetates

Boron enolates derived from α-heterosubstituted thioacetates and bearing menthonederived chiral ligands reacts with aldehydes to give anti aldols with excellent diastereo- and enantiocontrol.

The E/Z geometry of the enolate component determines face selection of the aldehyde component in chiral diazaborolidine-directed enantioselective aldol coupling

An analysis of the effect of enolate geometry on transition-state energy explains the stereochemistry of aldol reactions of acetate and propionate esters with aldehydes using as reagent the chiral diazaborolidine 1.

The catalytic asymmetric aldol reaction of aldehydes with unsubstituted and monosubstituted silyl ketene acetals: Formation of anti-β-hydroxy-α-methyl esters

The title rection with unsubstituted and monosubstituted silyl ketene acetals proceeds with high enantioselectivity, and in the latter case good diastereoselectivity favoring the anti-β-hydroxy-α-methyl esters in all reported cases.

Asymmetric Aldol Reaction between Achiral Silyl Enol Ethers and Achiral Aldehydes by Use of a Chiral Promoter System

In the presence of a chiral promoter consisting of tin(II) triflate, a chiral diamine, and tributyltin fluoride, the silyl enol ether of S-ethyl ethanethioate or S-tert-butyl ethanethioate reacts with aldehydes to afford the corresponding aldol-type adduc

New role of tin(II) compounds in organic synthesis

Three new carbon-carbon bond forming reactions by the use of new catalyst systems involving tin(II) compounds are described in this article.The aldol reaction of silyl enol ethers with acetals or aldehydes and the Michael reaction of silyl enol ethers wit