The Journal of organic chemistry

P (i-PrNCH2CH2) 3N: Efficient Catalyst for Synthesizing β-Hydroxyesters and α, β-Unsaturated Esters using α-Trimethylsilylethylacetate (TMSEA)

K Wadhwa, JG Verkade

Index: Wadhwa, Kuldeep; Verkade, John G. Journal of Organic Chemistry, 2009 , vol. 74, # 11 p. 4368 - 4371

Full Text: HTML

Citation Number: 28

Abstract

We present an efficient synthesis of β-hydroxyesters and α, β-unsaturated esters via activation of the silicon− carbon bond of α-trimethylsilylethylacetate using catalytic amounts of the commercially available P (i-PrNCH2CH2) 3N 1a. Selectivity for either of these two products can be achieved simply by altering the catalyst loading and reaction temperature to afford addition or stereoselective condensation. This method is mild and tolerates a wide ...

Related Articles:

The asymmetric synthesis of β-aryl-α-hydroxy esters from β-aryl-α, β-dihydroxy esters

[Lawrence, Nicholas J; Brown, Stephen Tetrahedron, 2002 , vol. 58, # 3 p. 613 - 619]

Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues

[Prashanth; Revanasiddappa, Hosakere D.; Lokanatha Rai; Veeresh Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 23 p. 7065 - 7070]

Diazo Reagents in Copper (I)??Catalyzed Olefination of Aldehydes

[Lebel, Helene; Davi, Michael Advanced Synthesis and Catalysis, 2008 , vol. 350, # 14-15 p. 2352 - 2358]

Amine??and Sulfonamide??Promoted Wittig Olefination Reactions in Water

[McNulty, James; McLeod, David Chemistry - A European Journal, 2011 , vol. 17, # 32 p. 8794 - 8798]

Synthesis and SAR investigation of natural phenylpropene-derived methoxylated cinnamaldehydes and their novel Schiff bases as potent antimicrobial and …

[Sharma, Upendra K.; Sood, Swati; Sharma, Nandini; Rahi, Praveen; Kumar, Rakesh; Sinha, Arun K.; Gulati, Arvind Medicinal Chemistry Research, 2013 , vol. 22, # 11 p. 5129 - 5140]

More Articles...