DC Field | Value | Language |
---|---|---|
dc.contributor.author | Kim, BM | ko |
dc.contributor.author | Kim, Hyunwoo | ko |
dc.contributor.author | Kim, WS | ko |
dc.contributor.author | Im, KY | ko |
dc.contributor.author | Park, JK | ko |
dc.date.accessioned | 2013-03-04T13:31:30Z | - |
dc.date.available | 2013-03-04T13:31:30Z | - |
dc.date.created | 2012-02-06 | - |
dc.date.created | 2012-02-06 | - |
dc.date.created | 2012-02-06 | - |
dc.date.issued | 2004-07 | - |
dc.identifier.citation | JOURNAL OF ORGANIC CHEMISTRY, v.69, no.15, pp.5104 - 5107 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10203/82791 | - |
dc.description.abstract | New chiral hydroxyethers 1a-f were prepared for asymmetric protonation of achiral enolates prepared from prochiral ketones. The enantioselectivity of protonation was highly dependent upon the acidity of the chiral alcohols, the highest enantioselectivity (90% ee) being achieved with 3,5-dichloro-substituted beta-hydroxyether 1c. A salt-free enolate generated from trimethylsilyl enol ether 4 provided product of the highest ee. Unlike other reagents, chloro-substituted alcohols provided almost consistent enantioselections throughout the reaction temperatures examined (-25 to -98 degreesC). Protonation of other aromatic ketones showed selectivity similar to that of 2-methyl-1-tetralone. | - |
dc.language | English | - |
dc.publisher | Amer Chemical Soc | - |
dc.title | Asymmetric protonation of ketone enolates using chiral beta-hydroxyethers: Acidity-tuned enantioselectivity | - |
dc.type | Article | - |
dc.identifier.wosid | 000222760600034 | - |
dc.identifier.scopusid | 2-s2.0-3543001063 | - |
dc.type.rims | ART | - |
dc.citation.volume | 69 | - |
dc.citation.issue | 15 | - |
dc.citation.beginningpage | 5104 | - |
dc.citation.endingpage | 5107 | - |
dc.citation.publicationname | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.identifier.doi | 10.1021/jo0498258 | - |
dc.contributor.localauthor | Kim, Hyunwoo | - |
dc.contributor.nonIdAuthor | Kim, BM | - |
dc.contributor.nonIdAuthor | Kim, WS | - |
dc.contributor.nonIdAuthor | Im, KY | - |
dc.contributor.nonIdAuthor | Park, JK | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | ALPHA-SULFINYL ALCOHOLS | - |
dc.subject.keywordPlus | ENANTIOFACE-DIFFERENTIATING PROTONATION | - |
dc.subject.keywordPlus | STEREOSELECTIVE PROTONATION | - |
dc.subject.keywordPlus | LITHIUM BROMIDE | - |
dc.subject.keywordPlus | GAMMA-HYDROXYSELENOXIDES | - |
dc.subject.keywordPlus | SUBSTITUTED KETONES | - |
dc.subject.keywordPlus | SAMARIUM ENOLATE | - |
dc.subject.keywordPlus | CARBANIONS | - |
dc.subject.keywordPlus | LACTONE | - |
dc.subject.keywordPlus | BENZYLATION | - |
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