1038432-31-3

Upstream product

• 1038432-24-4 (±)-methyl 2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoate 

Downstream Products

• 1038432-36-8 (+/-)-1-[(tert-butyldimethylsilyl)oxy]-1-(3-chlorophenyl)propan-2-one 
• 34841-39-9 bupropion 
• 857233-13-7 1-(3-chlorophenyl)-1-hydroxy-2 propanone 
• 152943-33-4 (+/-)-1-(3-chlorophenyl)-2-hydroxypropan-1-one 
• 1262890-52-7 4-[hydroxy(3-chlorophenyl)methyl]-1,3-oxazolidin-2-one 
• 1262890-54-9 C₁₄H₂₀ClNO₄ 
• 1262890-48-1 tert-butyl [2-(3-chlorophenyl)-2-tert-butyl-dimethyl-silanyloxy-1-(hydroxymethyl)ethyl]carbamate 

Relevant academic research and scientific papers

Diastereoselective approach to substituted oxazolidinones from Morita-Baylis-Hillman adducts

We disclose herein a new strategy for the diastereoselective preparation of 4- and 4,5-substituted oxazolidinones from Morita-Baylis-Hillman adducts. The strategy is based on an intramolecular cyclization involving a nucleophilic attack of an alkoxide ion

Hyphenating the curtius rearrangement with morita-baylis-hillman adducts: Synthesis of biologically active acyloins and vicinal aminoalcohols

Using Morita-Baylis-Hillman adducts as substrates, the Curtius rearrangement was performed in a sequence that allowed the synthesis of several hydroxy-ketones (acyloins) with great structural diversity and in good overall yields. These acyloins in turn were easily transformed into 1,2-anti aminoalcohols through a highly diastereoselective reductive amination step. The synthetic utility of these approaches was exemplified by performing the syntheses of (±)-bupropion, a drug used to treat the abstinence syndrome of smoker and (±)-spisulosine, a potent anti-tumoral compound originally isolated form a marine source.

Acyloins from Morita-Baylis-Hillman adducts: an alternative approach to the racemic total synthesis of bupropion

In this Letter, we describe an easy and straightforward strategy for the preparation of acyloins (α-hydroxyketones) from Morita-Baylis-Hillman adducts, based on a Curtius rearrangement. Different acyloins were obtained with good overall yield (>40% for three steps). To exemplify the synthetic usefulness of this strategy, total synthesis of (±)-bupropion, a dopamine, and nor-epinefrine reuptake inhibitor has been accomplished in eight steps with an overall yield of 25%.