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

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...

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Veröffentlicht in:	Journal of organic chemistry 2009-06, Vol.74 (11), p.4368-4371
Hauptverfasser:	Wadhwa, Kuldeep, Verkade, John G
Format:	Artikel
Sprache:	eng
Schlagworte:	Amines - chemistry Catalysis Catalysts: preparations and properties Chemistry Esters - chemical synthesis Exact sciences and technology General and physical chemistry Heterocyclic compounds Miscellaneous Organic chemistry Phosphorus Compounds - chemistry Preparations and properties Silanes - chemistry Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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container_issue	11
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container_title	Journal of organic chemistry
container_volume	74
creator	Wadhwa, Kuldeep Verkade, John G
description	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 array of functional groups.
doi_str_mv	10.1021/jo900477q
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Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wadhwa, Kuldeep</creatorcontrib><creatorcontrib>Verkade, John G</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wadhwa, Kuldeep</au><au>Verkade, John G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>P(i-PrNCH2CH2)3N: Efficient Catalyst for Synthesizing β-Hydroxyesters and α,β-Unsaturated Esters using α-Trimethylsilylethylacetate (TMSEA)</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-06-05</date><risdate>2009</risdate><volume>74</volume><issue>11</issue><spage>4368</spage><epage>4371</epage><pages>4368-4371</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><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 array of functional groups.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19402695</pmid><doi>10.1021/jo900477q</doi><tpages>4</tpages></addata></record>
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subjects	Amines - chemistry Catalysis Catalysts: preparations and properties Chemistry Esters - chemical synthesis Exact sciences and technology General and physical chemistry Heterocyclic compounds Miscellaneous Organic chemistry Phosphorus Compounds - chemistry Preparations and properties Silanes - chemistry Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
title	P(i-PrNCH2CH2)3N: Efficient Catalyst for Synthesizing β-Hydroxyesters and α,β-Unsaturated Esters using α-Trimethylsilylethylacetate (TMSEA)
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