Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of alpha-Halo Thioesters and Enolizable Aldehydes

doi:doi:10.1021/ja1057407

dc.contributor.author	Sauer, Scott	en_US
dc.contributor.author	Garnsey, Michelle R.	en_US
dc.contributor.author	Coltart, Dr Don	en_US
dc.date.accessioned	2011-06-21T17:26:22Z
dc.date.available	2011-06-21T17:26:22Z
dc.date.issued	2010	en_US
dc.identifier.citation	Sauer,Scott J.;Garnsey,Michelle R.;Coltart,Don M.. 2010. Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of alpha-Halo Thioesters and Enolizable Aldehydes. Journal of the American Chemical Society 132(40): 13997-13999.	en_US
dc.identifier.issn	0002-7863	en_US
dc.identifier.uri	http://hdl.handle.net/10161/4045
dc.description.abstract	The direct addition of enolizable aldehydes and a-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.	en_US
dc.language.iso	en_US	en_US
dc.publisher	AMER CHEMICAL SOC	en_US
dc.relation.isversionof	doi:10.1021/ja1057407	en_US
dc.subject	trifluoroethyl thioesters	en_US
dc.subject	polyketide synthases	en_US
dc.subject	ketones	en_US
dc.subject	triethylamine	en_US
dc.subject	bases	en_US
dc.subject	chemistry, multidisciplinary	en_US
dc.title	Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of alpha-Halo Thioesters and Enolizable Aldehydes	en_US
dc.title.alternative		en_US
dc.description.version	Version of Record	en_US
duke.date.pubdate	2010-10-13	en_US
duke.description.endpage	13999	en_US
duke.description.issue	40	en_US
duke.description.startpage	13997	en_US
duke.description.volume	132	en_US
dc.relation.journal	Journal of the American Chemical Society	en_US