72691-74-8

Upstream product

• 186581-53-3 diazomethane 
• 34713-70-7 2-Phenylpropanal 
• 72507-50-7 2-methyl-2-(trimethylsilyloxy)-3-pentanone 
• 67-56-1 methanol 
• 116616-48-9 4,4-Dibutyl-3-(3-hydroxy-2-methyl-4-phenylvaleryl)-5,5-pentamethylene-2-oxazolidone 
• 128999-78-0 (3S,4R)-3-Hydroxy-2-methylene-4-phenyl-pentanoic acid methyl ester 
• 89996-91-8 methyl (E)-2-methyl-4-phenyl-2-pentenecarboxylate 
• 124-41-4 sodium methylate 
• 72523-87-6 (2SR,3RS,4SR)-phenyl-3-hydroxy-2-methylpentanoic acid 

Relevant academic research and scientific papers

HIGHLY STEREOSELECTIVE REFORMATSKY REACTIONS OF 3-(2-BROMOPROPIONYL)-2-OXAZOLIDONE DERIVATIVES WITH VARIOUS ALDEHYDES

The Reformatsky reactions of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes were investigated to elucidate the effects of substituents in the 2-oxazolidone moieties on their diastereoselectivities.The highest 2,3-syn-diastereoselect

Regio- and Diastereoselective Ene Reactions of Singlet Oxygen with Dialkyl-Substituted Acrylic Esters

Photooxygenation of methyl (E)- and (Z)-2-methyl-4-phenyl-2-pentenecarboxylates (E-1, Z-1) afforded the hydroperoxy esters (R*,R*)-2a and (S*,S*)-2b through regiospecific and diastereoselective ene reaction of s

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.

A HIGHLY STEREOSELECTIVE SYNTHESIS OF ALDOLS EMPLOYING THE REFORMATSKY REACTION OF 3-(2-BROMOPROPIONYL)-2-OXAZOLIDONE DERIVATIVES WITH VARIOUS ALDEHYDES

The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2).While a 2,3-syn-3,4-syn-aldol could be sim

DIASTEREOFACIAL SELECTIVITY VIA ALDOL REACTIONS USING ETHYL DITHIOACETATE AND ETHYL DITHIOPROPIONATE ENOLATES

The lithium enolate of ethyl dithioacetate reacts with α-methyl aldehydes to yield the aldol products in which the syn configuration in the positions β and γ to the thiocarbonyl of the product is favored over the anti configuration.This selectivity is solvent-dependent, and is enhanced at lower temperatures.In most cases, syn:anti product ratios obtained under these conditions varied from 57:43 to >99:1, depending upon the structure of the α-methyl aldehyde.When the lithium enolate of ethyl dithiopropionate was allowed to react with α-methyl aldehydes, only two out of the four possible diastereomers were detected in the product mixtures.

Acyclic Stereoselection. 7. Stereoselective Synthesis of 2-Alkyl-3-hydroxy Carbonyl Compounds by Aldol Condensation

The stereochemistry of the aldol condensation of preformed lithium enolates of a variety of ethyl ketones and propionic acid derivatives with aldehydes has been investigated.It is found that certain compounds give completely or nearly completely one diastereomeric enolate and that the stereostructure of the resulting aldol is correlated with the stereostructure of the enolate from which is formed.The observed stereochemistry may be understood in terms of an ordered transition state in which both oxygens are oriented in more or less the same direction.It is shown that the observed stereochemistry is kinetically controlled.In many cases, the initial aldol adduct equilibrates to furnish predominantly a threo isomer.The rate of equilibration varies widely, ranging from very fast at -60 deg C with the propiophenone-benzaldehyde adduct to slow at 25 deg C for the ethyl tert-butyl ketone-benzaldehyde adduct.The equilibration behavior of lithium ketolates is compared with that of zinc ketolates, and some differences are noted.A method for achieving erythro-threo equilibration via a chloral hemiacetal is presented.A new reagent is introduced (trimethylsilyloxy ketone 36) which may be used to stereoselectively homologate an aldehyde to an erythro α-methyl-β-hydroxy acid.As an application of the use of stereoselective aldol condensations in synthesis, (+/-)-ephedrine (48) has been synthesized from benzaldehyde in 71 percent overall yield.