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Article: 1994 Merck Frosst Award Lecture new strategies for the stereoselective synthesis of natural and unnatural products via organometallic reagents and catalysts
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Title1994 Merck Frosst Award Lecture new strategies for the stereoselective synthesis of natural and unnatural products via organometallic reagents and catalysts
 
AuthorsLautens, M1
Ren, Y1
Delanghe, P1
Chiu, P1
Ma, S1
Colucci, J1
 
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
 
CitationCanadian Journal Of Chemistry, 1995, v. 73 n. 8, p. 1251-1257 [How to Cite?]
DOI: http://dx.doi.org/10.1139/v95-153
 
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.
 
ISSN0008-4042
2012 Impact Factor: 0.964
2012 SCImago Journal Rankings: 0.511
 
DOIhttp://dx.doi.org/10.1139/v95-153
 
DC FieldValue
dc.contributor.authorLautens, M
 
dc.contributor.authorRen, Y
 
dc.contributor.authorDelanghe, P
 
dc.contributor.authorChiu, P
 
dc.contributor.authorMa, S
 
dc.contributor.authorColucci, J
 
dc.date.accessioned2012-10-08T03:08:10Z
 
dc.date.available2012-10-08T03:08:10Z
 
dc.date.issued1995
 
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.
 
dc.description.natureLink_to_subscribed_fulltext
 
dc.identifier.citationCanadian Journal Of Chemistry, 1995, v. 73 n. 8, p. 1251-1257 [How to Cite?]
DOI: http://dx.doi.org/10.1139/v95-153
 
dc.identifier.doihttp://dx.doi.org/10.1139/v95-153
 
dc.identifier.epage1257
 
dc.identifier.issn0008-4042
2012 Impact Factor: 0.964
2012 SCImago Journal Rankings: 0.511
 
dc.identifier.issue8
 
dc.identifier.scopuseid_2-s2.0-0028820203
 
dc.identifier.spage1251
 
dc.identifier.urihttp://hdl.handle.net/10722/167532
 
dc.identifier.volume73
 
dc.languageeng
 
dc.publisherNRC Research Press. The Journal's web site is located at http://pubs.nrc-cnrc.gc.ca/cgi-bin/rp/rp2_desc_e?cjc
 
dc.publisher.placeCanada
 
dc.relation.ispartofCanadian Journal of Chemistry
 
dc.subjectMethylenecyclopropane
 
dc.subjectNickel
 
dc.subjectOxabicyclic
 
dc.subjectPalladium
 
dc.subjectStereocontrol
 
dc.title1994 Merck Frosst Award Lecture new strategies for the stereoselective synthesis of natural and unnatural products via organometallic reagents and catalysts
 
dc.typeArticle
 
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<item><contributor.author>Lautens, M</contributor.author>
<contributor.author>Ren, Y</contributor.author>
<contributor.author>Delanghe, P</contributor.author>
<contributor.author>Chiu, P</contributor.author>
<contributor.author>Ma, S</contributor.author>
<contributor.author>Colucci, J</contributor.author>
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<description.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.</description.abstract>
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<subject>Methylenecyclopropane</subject>
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<subject>Oxabicyclic</subject>
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Author Affiliations
  1. University of Toronto