Linked Life Data

12590513

Source:http://linkedlifedata.com/resource/pubmed/id/12590513

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
8
pubmed:dateCreated
2003-2-19
pubmed:abstractText
Access to stereochemically complex, polyfunctionalized amine derivatives is made possible using novel oxathiazinane N,O-acetal starting materials. These heterocycles are prepared through intramolecular sulfamate ester C-H insertion with a Rh(2+)-carboxylate catalyst and PhI(OAc)(2) as the terminal oxidant. Such compounds function as unique iminium ion equivalents to which nucleophilic alkynylzinc reagents add smoothly in the presence of BF(3).OEt(2). The coupled products are isolated in high yield (63-92%) and with good levels of diastereoinduction (6 --> 20:1). The alkyne-substituted oxathiazinanes serve as versatile building blocks and may be further manipulated through nucleophilic ring-opening reactions of the sulfamate core. The efficient construction of 1,7,8-trihydroxyindolizidine in six steps and in 34% overall yield highlights the power of these combined methods for synthesis.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Feb
pubmed:issn
0002-7863
pubmed:author
pubmed:issnType
Print
pubmed:day
26
pubmed:volume
125
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
2028-9
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
2003
pubmed:articleTitle
Novel iminium ion equivalents prepared through C-H oxidation for the stereocontrolled synthesis of functionalized propargylic amine derivatives.
pubmed:affiliation
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't