108864-69-3

Upstream product

• 74130-31-7 3-(benzyloxy)-2-methylpropanal 
• 15681-48-8 lithium dimethylcuprate 
• 108815-13-0 (2S,3R)-2-methyl-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)butan-1-ol 
• 100-39-0 benzyl bromide 
• 90026-43-0 (2R,3S)-2-methylbutane-1,3-diol 
• 108763-86-6 ethyl (2R,3R)-2-methyl-3-tetrahydropyranyloxybutanoate 
• 108763-87-7 (2S,3R)-2-methylbutane-1,3-diol 1-benzyl,3-THP-ether 
• 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 
• 917-64-6 methyl magnesium iodide 
• 176848-43-4 rac-4-(benzyloxy)-3-methylbutan-2-one 

Downstream Products

• 108864-70-6 (2S,3S)-2-methylbutan-1,3-diol 1-benzyl ether 
• 108763-89-9 (2S,3S)-3-t-butyldimethylsilyloxy-2-methylbutan-1-ol benzyl ether 
• 108763-88-8 (2S,3S)-3-(3',5'-dinitrobenzoyloxy)-2-methylbutan-1-ol benzyl ether 

Relevant academic research and scientific papers

Preparation of Optically Enriched Secondary Alkyllithium and Alkylcopper Reagents—Synthesis of (?)-Lardolure and Siphonarienal

Optically enriched secondary alkyl iodides were converted into secondary alkyllithium and secondary alkylcopper compounds with very high retention of configuration. Quenching with various electrophiles, including chiral epoxides, provided a range of chira

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.

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.

SYNTHESIS OF (2S,3R,1'R)-STEGOBINONE, THE PHEROMONE OF THE DRUGSTORE BEETLE, WITH STEREOCONTROL AT C-2 AND C-1'

(2S,3R,1'R)-Stegobinone , the pheromone of Stegobium paniceum L., was synthesized with stereocontrol at C-2 and C-1' starting from ethyl (R)-3-hydroxybutanoate and methyl (R)-3-hydroxy-

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.