74263-03-9

Upstream product

• 53346-05-7 2-(benzyloxy)propanal 
• 71821-69-7 1-(triethylsilyl)propan-1-one 
• 74262-58-1 4-benzyloxy-2-methylpent-2-ene 
• 100-39-0 benzyl bromide 
• 131793-65-2 N-<(2R,3R,4S)-4-(benzyloxy)-3-hydroxy-2-methylpentanoyl>-(1R,2S,6R,7S)-1,10,10-trimethyl-4-oxo-5-aza-3-oxatricyclo<5.2.1.0^2,6>decane 
• 72507-50-7 2-methyl-2-(trimethylsilyloxy)-3-pentanone 

Downstream Products

• 102285-96-1 (4S,5S,6S)-6-(benzyloxy)-5-hydroxy-2,4-dimethylheptan-3-one 
• 102341-06-0 (4R,5R,6S)-6-(bnezyloxy)-5-hydroxy-2,4-dimethylheptan-3-one 
• 102285-98-3 (1'S,4S,5R,6R)-4-<1-(benzyloxy)ethyl>-6-phenyl-2,2,5-trimethyl-1,3-dioxane 
• 102285-97-2 (1R,2R,3S,4S)-4-(benzyloxy)-2-methyl-1-phenylpentane-1,3-diol 
• 102341-04-8 (1S,2R,3S,4S)-4-Benzyloxy-2-methyl-1-phenyl-pentane-1,3-diol 
• 94233-75-7 (2R,3R,4S)-4-(bnezyloxy)-3-hydroxy-2-methyl-1-phenylpentan-1-one 
• 94233-76-8 (2S,3S,4S)-4-(benzyloxy)-3-hydroxy-2-methyl-1-phenylpentan-1-one 

Relevant academic research and scientific papers

Asymmetric aldol reactions. A new camphor-derived chiral auxiliary giving highly stereoselective aldol reactions of both lithium and titanium(IV) enolates

A new, conformationally rigid camphor-derived N-propionyloxazolidinone effects asymmetric stereochemical control in syn-selective aldol condensations of the derived lithium and titanium(IV) enolates with a variety of aldehydes. Simple and diastereofacial selectivities of the reaction are high, and diastereomeric purities of the crude aldol adducts can be improved, usually by a single recrystallization, to levels of 98-99% in most cases. The observed facial selectivity is best explained by a transition structure in which intramolecular chelation between the oxazolidinone carbonyl oxygen and the metal induces an enolate π-facial differentiation; the major products observed are those expected from chelation control. Hydrolysis of the exocyclic carbonyl of the aldol adducts led to β-hydroxy-α-methylcarboxylic acids, with recovery of the chiral auxiliary. Consonant double-asymmetric induction with (R)-2-(benzyloxy)propanal gave the product expected from oxazolidinone chelation but nonchelation of the aldehyde benzyloxy group.

Acyl Silanes. Reagents for Diastereoselective Aldol Condensations

The acyl silanes 4a-c have been prepared and the stereochemistry of their aldol reactions with aldehydes have been investigated; the β-hydroxy ketones obtained were transformed into β-hydroxy acids by simple oxidation with basic hydrogen peroxide.

Acyclic Stereoselection. 9. Stereochemistry of the Addition of Lithium Enolates to α-Alkoxy Aldehydes

The stereochemistry of addition of lithium enolates derived from esters and ketones to the α-alkoxy aldehydes 1-5 has been investigated.In all cases, the predominant product is that predicted by application of Felkin's model for asymmetric induction and by assuming the alkoxy group to be the "large" group.The Cram cyclic model for asymmetric induction is not followed.Stereostructures have been assigned by a combination of conversion to products of known stereostructure, 13C and 1H NMR correlations, and single-crystal X-ray analysis.