16897-88-4

Upstream product

• 176848-43-4 rac-4-(benzyloxy)-3-methylbutan-2-one 
• 917-64-6 methyl magnesium iodide 
• 74130-31-7 3-(benzyloxy)-2-methylpropanal 
• 73255-29-5 3-(hydroxymethyl)but-3-en-2-one 
• 82167-79-1 (-)-(R)-4-benzyloxy-3-methylbutan-2-one 
• 100-51-6 benzyl alcohol 
• 603040-96-6 C₁₉H₂₂O₃ 
• 78088-28-5 ethyl (+/-)-(2R,3R)-3-hydroxy-2-methylbutanoate 
• 27942-89-8 5-methyl-2-phenyl-[1,3]dioxane 
• 100-52-7 benzaldehyde 
• 63930-46-1 3-(benzyloxy)-2-methylpropan-1-ol 
• 15681-48-8 lithium dimethylcuprate 

Downstream Products

• 603040-97-7 C₂₀H₂₆O₃ 

Relevant academic research and scientific papers

Stereoselective Synthesis and Retentive Trapping of α-Chiral Secondary Alkyllithiums Leading to Stereodefined α,β-Dimethyl Carboxylic Esters

The treatment of α-chiral secondary alkyl iodides with tBuLi at ?100 °C leads to the corresponding secondary alkyllithiums with high retention of configuration. Subsequent quenching with various electrophiles such as Bu2S2, DMF, MeOB(OR)2, or Et2CO provides the desired products with retention of configuration. Furthermore, a transmetalation with CuBr?P(OEt)3also allows retentive trapping with acid chlorides and ethylene oxide. The quenching of the resulting alkyllithiums with ClCO2Et furnishes stereoselectively syn- and anti-ethyl-2,3-dimethyl ester carboxylates (d.r.>94 %). Related esters bearing three adjacent stereo-controlled centers (stereotriads) have also been prepared. This method has been applied to the synthesis of the ant pheromone (±)-lasiol in 26 % overall yield (four steps) with d.r.=97:3 starting from commercially available cis-2,3-epoxybutane.

Lewis Base–Br?nsted Acid–Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses

Establishing one-pot, multi-step protocols combining different types of catalysts is one important goal for increasing efficiency in modern organic synthesis. In particular, the high potential of biocatalysts still needs to be harvested. Based on an in-depth mechanistic investigation of a new organocatalytic protocol employing two catalysts {1,4-diazabicyclo[2.2.2]octane (DABCO); benzoic acid (BzOH)}, a sequence was established providing starting materials for enzymatic refinement (ene reductase; alcohol dehydrogenase): A gram-scale access to a variety of enantiopure key building blocks for natural product syntheses was enabled utilizing up to six catalytic steps within the same reaction vessel.

MACROCYCLIC COMPOUNDS USEFUL AS PHARMACEUTICALS

The present invention provides compounds having formula (I), and additionally provides methods for the synthesis thereof and methods for the use thereof in the treatment of various disorders including inflammatory or autoimmune disorders, and disorders involving malignancy or increased angiogenesis, wherein R1 -R11, t, X, Y, Z, and n are as defined herein.

Chemoenzymatic Approach toward the Pure Enantiomers of 2-Methyl-1,3-propanediol Mono(p-Methoxybenzyl Ether)

In a route towards the enantiomerically pure 2-methylpropane-1,3-diol mono(p-methoxybenzyl ether), which is an important starting material for natural product synthesis, a kinetic resolution approach by means of lipase-catalyzed hydrolysis as well as acyl

Chelation-controlled reduction of α- and β-oxygenated ketones with lithium tri-n-butylborohydride

Lithium tri-n-butyl borohydride showed high selectivity in the reduction of α- and β-oxygenated ketones, giving a preponderance of the chelation controlled products.

CHELATION-CONTROLLED NUCLEOPHILIC ADDITIONS. 2. A HIGHLY EFFECTIVE SYSTEM FOR ASYMMETRIC INDUCTION IN THE REACTION ON ORGANOMETALLIC WITH β-ALKOXYALDEHYDES.

Organocuprates have been found to be highly stereoselective reagents for the addition of carbanionic nucleophiles to α-asymmetric aldehydes bearing β-oxigen substituents.The major products are those predicted by a chelation-controlled transition state and have diastereomeric purities ranging from 15-30:1.