Linked Life Data

16277518

Source:http://linkedlifedata.com/resource/pubmed/id/16277518

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
45
pubmed:dateCreated
2005-11-9
pubmed:abstractText
A new protocol for the synthesis of vicinal amino alcohols is described. The method employs a Barbier-type reaction between an imine and 3-benzoyloxyallyl bromide in the presence of zinc metal. The addition products are debenzoylated to afford amino alcohols in good yields and with diastereomeric ratios greater than 85:15 in favor of the anti isomer. A Hammett study has been performed which strongly indicates that the allylation does not follow a radical mechanism, but instead an organometallic reagent is formed which subsequently reacts with the imine. A computational study based on this mechanism reproduces the observed diastereoselectivity with high accuracy, but only when a sufficiently large portion of the substrate is included.
pubmed:language
eng
pubmed:journal
pubmed:status
PubMed-not-MEDLINE
pubmed:month
Nov
pubmed:issn
0002-7863
pubmed:author
pubmed:issnType
Print
pubmed:day
16
pubmed:volume
127
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
15756-61
pubmed:year
2005
pubmed:articleTitle
Nonradical zinc-Barbier reaction for diastereoselective synthesis of vicinal amino alcohols.
pubmed:affiliation
Center for Sustainable and Green Chemistry, Department of Chemistry, Technical University of Denmark, Building 201, Kemitorvet, DK-2800 Lyngby, Denmark.
pubmed:publicationType
Journal Article