|
rdf:type |
|
|
lifeskim:mentions |
|
|
pubmed:issue |
24
|
|
pubmed:dateCreated |
2007-11-16
|
|
pubmed:abstractText |
The development of a diastereoselective, three-step strategy for the construction of substituted tetrahydrofurans from alkenyl aldehydes based on the tandem Mukaiyama aldol-lactonization process and Mead reductive cyclization of keto beta-lactones is reported. Stereochemical outcomes of the TMAL process are consistent with models established for Lewis acid-mediated additions to alpha-benzyloxy and beta-silyloxy aldehydes while reductions of the five-membered oxocarbenium ions are consistent with Woerpel's models. Further rationalization for observed high diastereoselectivity in reductions of alpha-silyloxy 5-membered oxocarbenium ions based on stereoelectronic effects are posited. A diagnostic trend for coupling constants of gamma-benzyloxy beta-lactones was observed that should enable assignment of the relative configuration of these systems.
|
|
pubmed:grant |
|
|
pubmed:commentsCorrections |
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-10814287,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-10814351,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-11405752,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-11592906,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-12227756,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-12465976,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-12769572,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-12968864,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-14664599,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-15174834,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-15469369,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-15844912,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-15884928,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-16076173,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-16076193,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-16146398,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-16288541,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-16351047,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-16756287,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-16956227,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17973527-16986934
|
|
pubmed:language |
eng
|
|
pubmed:journal |
|
|
pubmed:citationSubset |
IM
|
|
pubmed:chemical |
|
|
pubmed:status |
MEDLINE
|
|
pubmed:month |
Nov
|
|
pubmed:issn |
0022-3263
|
|
pubmed:author |
|
|
pubmed:issnType |
Print
|
|
pubmed:day |
23
|
|
pubmed:volume |
72
|
|
pubmed:owner |
NLM
|
|
pubmed:authorsComplete |
Y
|
|
pubmed:pagination |
9053-9
|
|
pubmed:dateRevised |
2011-5-16
|
|
pubmed:meshHeading |
|
|
pubmed:year |
2007
|
|
pubmed:articleTitle |
Diastereoselective synthesis of tetrahydrofurans via mead reductive cyclization of keto-beta-lactones derived from the tandem Mukaiyama aldol lactonization (TMAL) process.
|
|
pubmed:affiliation |
Department of Chemistry, Texas A&M University, College Station, TX 77842-3012, USA.
|
|
pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't,
Research Support, N.I.H., Extramural
|
