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Article: Chiral auxiliaries for asymmetric radical cyclization reactions: Application to the enantioselective synthesis of (+)-triptocallol

TitleChiral auxiliaries for asymmetric radical cyclization reactions: Application to the enantioselective synthesis of (+)-triptocallol
Authors
Issue Date2001
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2001, v. 3 n. 1, p. 111-114 How to Cite?
Abstract(equation presented) A series of epimeric 8-aryl menthyl derivatives 5a-d and 6a-l, prepared from the same chiral source (R)-pulegone, were employed as chiral auxiliaries in the asymmetric radical cyclization reactions of β-keto esters mediated by Mn(OAc) 3. Chiral precursors 8c and 8d provided the cyclization products 10c and 10d, respectively, as single isomers (dr > 99:1), whereas the cyclization of precursor 9k gave 13k with good stereoselectivity (dr = 24:1). Diastereomer 13e was employed as the key intermediate in the enantioselective synthesis of (+)-triptocallol in 90% ee.
Persistent Identifierhttp://hdl.handle.net/10722/70223
ISSN
2015 Impact Factor: 6.732
2015 SCImago Journal Rankings: 3.187
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.contributor.authorXu, Men_HK
dc.contributor.authorBian, MYen_HK
dc.date.accessioned2010-09-06T06:20:52Z-
dc.date.available2010-09-06T06:20:52Z-
dc.date.issued2001en_HK
dc.identifier.citationOrganic Letters, 2001, v. 3 n. 1, p. 111-114en_HK
dc.identifier.issn1523-7060en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70223-
dc.description.abstract(equation presented) A series of epimeric 8-aryl menthyl derivatives 5a-d and 6a-l, prepared from the same chiral source (R)-pulegone, were employed as chiral auxiliaries in the asymmetric radical cyclization reactions of β-keto esters mediated by Mn(OAc) 3. Chiral precursors 8c and 8d provided the cyclization products 10c and 10d, respectively, as single isomers (dr > 99:1), whereas the cyclization of precursor 9k gave 13k with good stereoselectivity (dr = 24:1). Diastereomer 13e was employed as the key intermediate in the enantioselective synthesis of (+)-triptocallol in 90% ee.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.htmlen_HK
dc.relation.ispartofOrganic Lettersen_HK
dc.titleChiral auxiliaries for asymmetric radical cyclization reactions: Application to the enantioselective synthesis of (+)-triptocallolen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1523-7060&volume=3&issue=1&spage=111&epage=114&date=2001&atitle=Chiral+Auxiliaries+for+Asymmetric+Radical+Cyclization+Reactions:++Application+to+the+Enantioselective+Synthesis+of+(+)-Triptocallolen_HK
dc.identifier.emailYang, D:yangdan@hku.hken_HK
dc.identifier.authorityYang, D=rp00825en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ol0068243en_HK
dc.identifier.scopuseid_2-s2.0-0035843335en_HK
dc.identifier.hkuros58723en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0035843335&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume3en_HK
dc.identifier.issue1en_HK
dc.identifier.spage111en_HK
dc.identifier.epage114en_HK
dc.identifier.isiWOS:000166360000030-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridXu, M=15729771700en_HK
dc.identifier.scopusauthoridBian, MY=7003520492en_HK

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