Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of alpha-Halo Thioesters and Enolizable Aldehydes
| dc.contributor.author | Sauer, Scott J | |
| dc.contributor.author | Garnsey, Michelle R | |
| dc.contributor.author | Coltart, Don M | |
| dc.date.accessioned | 2011-06-21T17:26:22Z | |
| dc.date.available | 2011-06-21T17:26:22Z | |
| dc.date.issued | 2010 | |
| 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. | |
| dc.description.version | Version of Record | |
| 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. | |
| dc.identifier.issn | 0002-7863 | |
| dc.identifier.uri | ||
| dc.language.iso | en_US | |
| dc.publisher | American Chemical Society (ACS) | |
| dc.relation.isreplacedby | 10161/12403 | |
| dc.relation.isreplacedby | ||
| dc.relation.isversionof | 10.1021/ja1057407 | |
| dc.relation.journal | Journal of the American Chemical Society | |
| dc.subject | trifluoroethyl thioesters | |
| dc.subject | polyketide synthases | |
| dc.subject | ketones | |
| dc.subject | triethylamine | |
| dc.subject | bases | |
| dc.subject | chemistry, multidisciplinary | |
| dc.title | Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of alpha-Halo Thioesters and Enolizable Aldehydes | |
| dc.title.alternative | ||
| dc.type | Other article | |
| duke.date.pubdate | 2010-10-13 | |
| duke.description.issue | 40 | |
| duke.description.volume | 132 | |
| pubs.begin-page | 13997 | |
| pubs.end-page | 13999 |