File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: 1994 Merck Frosst Award Lecture new strategies for the stereoselective synthesis of natural and unnatural products via organometallic reagents and catalysts

Title1994 Merck Frosst Award Lecture new strategies for the stereoselective synthesis of natural and unnatural products via organometallic reagents and catalysts
Authors
KeywordsMethylenecyclopropane
Nickel
Oxabicyclic
Palladium
Stereocontrol
Issue Date1995
PublisherNRC Research Press. The Journal's web site is located at http://pubs.nrc-cnrc.gc.ca/cgi-bin/rp/rp2_desc_e?cjc
Citation
Canadian Journal Of Chemistry, 1995, v. 73 n. 8, p. 1251-1257 How to Cite?
Abstract
Samarium in the presence of diiodomethane selectively cyclopropanates an allenic alcohol to yield a methylenecyclopropane with modest to excellent diastereoselectivity. The effect of substituents at the carbinol carbon and the allenic carbon on the diastereoselectivity was investigated. A palladium catalyst was shown to promote the intramolecular cycloaddition of the methylenecyclopropane with an electron-deficient alkyne to yield a methylenecyclopentane. The reaction was stereospecific with retention of stereochemistry as proven by X-ray diffraction. Nickel catalysts accelerate the hydroalumination of oxabicyclo[3.2.1]alkenes, leading to bicyclic trialkylalanes. Upon treatment with a Lewis acid (diisobutylaluminum chloride), the trialkylalanes fragment to provide cycloheptenols. This reaction, followed by an enantioselective enzyme-catalyzed esterification, was used as a key step in a synthesis of the mevinic acid lactone.
Persistent Identifierhttp://hdl.handle.net/10722/167532
ISSN
2013 Impact Factor: 1.013
ISI Accession Number ID

 

Author Affiliations
  1. University of Toronto
DC FieldValueLanguage
dc.contributor.authorLautens, Men_US
dc.contributor.authorRen, Yen_US
dc.contributor.authorDelanghe, Pen_US
dc.contributor.authorChiu, Pen_US
dc.contributor.authorMa, Sen_US
dc.contributor.authorColucci, Jen_US
dc.date.accessioned2012-10-08T03:08:10Z-
dc.date.available2012-10-08T03:08:10Z-
dc.date.issued1995en_US
dc.identifier.citationCanadian Journal Of Chemistry, 1995, v. 73 n. 8, p. 1251-1257en_US
dc.identifier.issn0008-4042en_US
dc.identifier.urihttp://hdl.handle.net/10722/167532-
dc.description.abstractSamarium in the presence of diiodomethane selectively cyclopropanates an allenic alcohol to yield a methylenecyclopropane with modest to excellent diastereoselectivity. The effect of substituents at the carbinol carbon and the allenic carbon on the diastereoselectivity was investigated. A palladium catalyst was shown to promote the intramolecular cycloaddition of the methylenecyclopropane with an electron-deficient alkyne to yield a methylenecyclopentane. The reaction was stereospecific with retention of stereochemistry as proven by X-ray diffraction. Nickel catalysts accelerate the hydroalumination of oxabicyclo[3.2.1]alkenes, leading to bicyclic trialkylalanes. Upon treatment with a Lewis acid (diisobutylaluminum chloride), the trialkylalanes fragment to provide cycloheptenols. This reaction, followed by an enantioselective enzyme-catalyzed esterification, was used as a key step in a synthesis of the mevinic acid lactone.en_US
dc.languageengen_US
dc.publisherNRC Research Press. The Journal's web site is located at http://pubs.nrc-cnrc.gc.ca/cgi-bin/rp/rp2_desc_e?cjcen_US
dc.relation.ispartofCanadian Journal of Chemistryen_US
dc.subjectMethylenecyclopropaneen_US
dc.subjectNickelen_US
dc.subjectOxabicyclicen_US
dc.subjectPalladiumen_US
dc.subjectStereocontrolen_US
dc.title1994 Merck Frosst Award Lecture new strategies for the stereoselective synthesis of natural and unnatural products via organometallic reagents and catalystsen_US
dc.typeArticleen_US
dc.identifier.emailChiu, P:pchiu@hku.hken_US
dc.identifier.authorityChiu, P=rp00680en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1139/v95-153-
dc.identifier.scopuseid_2-s2.0-0028820203en_US
dc.identifier.volume73en_US
dc.identifier.issue8en_US
dc.identifier.spage1251en_US
dc.identifier.epage1257en_US
dc.identifier.isiWOS:A1995RZ49200002-
dc.publisher.placeCanadaen_US
dc.identifier.scopusauthoridLautens, M=26643350000en_US
dc.identifier.scopusauthoridRen, Y=55231121800en_US
dc.identifier.scopusauthoridDelanghe, P=6507408508en_US
dc.identifier.scopusauthoridChiu, P=11140148700en_US
dc.identifier.scopusauthoridMa, S=7403725552en_US
dc.identifier.scopusauthoridColucci, J=6701701396en_US

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats