137618-97-4

Upstream product

• 5077-67-8 1-Hydroxy-2-butanone 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 1226459-91-1 C₂₁H₂₈O₃Si 
• 169871-36-7 (4R,5R)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-hydroxymethyl-1,3-dioxolane 
• 1497395-96-6 (tert-butyl)(((4R,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)diphenylsilane 
• 91376-49-7 (S)-1-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-butene 

Downstream Products

• 139167-18-3 1-(tert-butyldiphenylsiloxy)-2-cyclopropylidenebutane 
• 137618-94-1 1-t-butyl-1,1-diphenyl-3,3,3-trimethyldisiloxane 
• 137618-91-8 2-(tert-Butyl-diphenyl-silanyloxymethyl)-2-trimethylsilanyloxy-butyronitrile 

Relevant academic research and scientific papers

A convergent approach for the total synthesis of the α-glucosidase inhibitor (-)-panaxjapyne-C

The stereoselective total synthesis of (-)-panaxjapyne-C was accomplished in a convergent fashion. The synthesis utilizes the readily available enantiomers l-(+)-diethyltartrate and d-(-)-diethyltartrate and involves a Cadiot-Chodkiewicz coupling reaction, and an Ohira-Bestmann reaction as the key steps.

Carbene-metal hydrides can be much less acidic than phosphine-metal hydrides: Significance in hydrogenations

Acidities of iridium hydride intermediates were shown to be critical in some transformations mediated by the chiral analogues of Crabtree's catalyst, 1-3. To do this, several experiments were undertaken to investigate the acidities of hydrogenation mixtures formed using these iridium-oxazoline complexes. DFT calculations indicated that the acidity difference for Ir-H intermediates in these hydrogenations were astounding; iridium hydride from the N-heterocyclic carbene catalyst 1 was calculated to be around seven pK a units less acidic than those from the P-based complexes 2 and 3. Consistent with this, the carbene complex 1 was shown to be more effective for hydrogenations of acid-sensitive substrates. In deuteration experiments, less "abnormal" deuteration was observed, corresponding to fewer complications from acid-mediated alkene isomerization preceding the D 2-addition step. Finally, simple tests with pH indicators provided visual evidence that phosphine-based catalyst precursors give significantly more acidic reaction mixtures than the corresponding N-heterocyclic carbene ones. These observations indicate carbene-for-phosphine (and similar) ligand substitutions may impact the outcome of catalytic reactions by modifying the acidities of the metal hydrides formed.

A Concise and Enantioselective Approach to Cyclobutanones by Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols. An Enantiocontrolled Synthesis of (+)- and (-)-α-Cuparenones

A tandem Katsuki-Sharpless asymmetric epoxidation and enantiospecific ring expansion of 2-alkyl(or 2-aryl)-2-cyclopropylideneethanols (1a-i) afforded chiral 1-alkyl(or 1-aryl)-1-(hydroxymethyl)cyclobutanones (3a-i) in high yields and high enantiomeric excess.These compounds are potentially valuable synthons for the enantioselective creation of the quaternary carbons.Hence, this enabled us to accomplish a concise and enantioselective total synthesis of both (+)- and (-)-cuparenones (11).

THE REACTION OF O-SILYLATED α-KETOLS WITH TRIMETHYLSILYL CYANIDE

The reactions of a series of O-silylated α-ketols with trimethylsilyl cyanide have been investigated.Formation of the expected O-trimethylsilyl cyanohydrins as major products has been shown to be accompanied by the hitherto unsuspected formation of a disi