Linked Life Data

12708844

Source:http://linkedlifedata.com/resource/pubmed/id/12708844

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
17
pubmed:dateCreated
2003-4-23
pubmed:abstractText
This communication describes a novel and general method for the alpha-regioselective prenylation of carbonyl compounds. This method which employs chiral gamma-prenyl-1,5 diol as the prenyl source using a catalytic amount of Lewis or Brønsted acid affords the products in excellent enantioselectivies (up to 98% ee) and good yields (up to 95% yield). Furthermore, the reaction is highly chemoselective, reacting selectively with the aldehyde without affecting the enone and the alpha,beta-unsaturated ester functionalities. Detailed mechanistic studies disclose the facile epimerization of aromatic alcohol in dichloromethane in the presence of In(OTf)3. The use of non-polar solvents such as hexane in the presence of In(OTf)3 or TfOH effectively suppresses this epimerization.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Apr
pubmed:issn
0002-7863
pubmed:author
pubmed:issnType
Print
pubmed:day
30
pubmed:volume
125
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
4990-1
pubmed:dateRevised
2008-1-17
pubmed:meshHeading
pubmed:year
2003
pubmed:articleTitle
A novel and general alpha-regioselective and highly enantioselective prenylation of aldehydes.
pubmed:affiliation
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't