221082-77-5

Upstream product

• 565-69-5 ethyl isopropyl ketone 
• 426833-06-9 1-benzyloxy-3,5-dimethylhexane-2,4-dione 
• 60656-87-3 benzyloxyacetoaldehyde 
• 642993-51-9 1-(1H-benzotriazol-1-yl)-2-benzyloxyethan-1-one 
• 30379-55-6 benzyloxyacetic acid 

Downstream Products

• 642993-59-7 (2S,3R,4R)-1-benzyloxy-2,4-bis(tert-butyldimethylsiloxy)-3,5-dimethylhexane 
• 642993-57-5 (-)-(4S,5R,6R)-4-benzyloxymethyl-6-isopropyl-2,2,5-trimethyl-1,3-dioxane 

Relevant academic research and scientific papers

Enantioselective synthesis of δ-/γ-alkoxy-β-hydroxy- α-alkyl-substituted Weinreb amides via DKR-ATH: Application to the synthesis of advanced intermediate of (-)-brevisamide

A method of preparing stereodefined δ-/γ-alkoxy-β-hydroxy- α-alkyl-substituted Weinreb amides containing two successive hydroxyl-alkyl stereocenters has been developed. Further, this strategy coupled with organo-catalyzed asymmetric epoxidation culminates in the synthesis of a critical intermediate of (-)-brevisamide and its diastereomers.

Enantioselective monoreduction of 2-alkyl 1,3-diketones using chiral ruthenium catalysts. Synthesis of the C14-C25 fragment of bafilomycin A 1

The enantioselective monoreduction of 2-alkyl 1,3-diketones by dynamic kinetic resolution using optically active ruthenium catalysts allowed the preparation of the C14-C25 fragment of bafilomycin A1.

Synthesis of the C14-C25 Subunit of Bafilomycin A1

The enantioselective synthesis of the C14-C25 subunit of bafilomycin A 1, was realized in a convergent route. The sequence involves two dynamic kinetic resolution steps of 2-alkyl 1,3-diketones that use optically active ruthenium complexes, an

Enantioselective Monoreduction of 2-Alkyl-1,3-diketones Mediated by Chiral Ruthenium Catalysts. Dynamic Kinetic Resolution

(Matrix Presented) The reduction of 2-alkyl-1,3-diketones using (R,R)- or (S,S)-RuCl[N-(tosyl)-1,2-diphenylethylenediamine](p-cymene) in the presence of formic acid and triethylamine affords syn-2-alkyl-3-hydroxy ketones as the major products with high en

C2-symmetric copper(II) complexes as Chiral Lewis acids. Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde

C2-Symmetric bis(oxazolinyl)pyridine (pybox)-Cu(II) complexes have been shown to catalyze enantioselective Mukaiyama aldol reactions between (benzyloxy)acetaldehyde and a variety of silylketene acetals. The aldol products are generated in high yields and in 92-99% enantiomeric excess using as little as 0.5 mol % of chiral catalyst [Cu((S,S)-Ph-pybox)](SbP6)2. With substituted silylketene acetals, syn reaction diastereo-selection ranging from 95:5 to 97:3 and enantioselectivities ≥95% are observed. Investigation into the reaction mechanism utilizing doubly labeled silylketene acetals indicates that the silyl-transfer step is intermolecular. Further mechanistic studies revealed a significant positive nonlinear effect, proposed to arise from the selective formation of the [Cu((S,S)-Ph-pybox)((R,R)-Ph-pybox)](SbF6)2 2:1 ligand:metal complex. A stereochemical model is presented in which chelation of (benzyloxy)acetaldehyde to the metal center to form a square pyramidal copper intermediate accounts for the observed sense of induction. Support for this proposal has been obtained from double stereodifferentiating reactions, EPR spectroscopy, ESI spectrometry, and, ultimately, the X-ray crystal structure of the aldehyde bound to the catalyst. The C2-symmetric bis(oxazolinyl)-Cu(II) complex [Cu((S,S)-tert-Bu-box)](OTf)2 is also an efficient catalyst for the aldol reaction, but the scope with this system is not as broad.