File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in Situ

TitleInvestigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in Situ
Authors
Issue Date2003
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2003, v. 68 n. 16, p. 6321-6328 How to Cite?
AbstractWe found that dioxiranes generated in situ from ketones 1-6 and Oxone underwent intramolecular oxidation of unactivated C-H bonds at δ sites of ketones to yield tetrahydropyrans. From the trans/cis ratio of oxidation products 1a and 2a as well as the retention of the configuration at the δ site of ketone 5, we proposed that the oxidation reaction proceeds through a concerted pathway under a spiro transition state. The intramolecular oxidation of ketone 6 showed the preference for a tertiary δ C-H bond over a secondary one. This intramolecular oxidation method can be extended to the oxidation of the tertiary γ′ C-H bond of ketones 9 and 10. For ketone 11 with two δ C-H bonds and one γ′ C-H bond linked respectively by a sp 3 hydrocarbon tether and a sp 2 ester tether, the oxidation took place exclusively at the δ C-H bonds. Finally, by introducing proper tethers, regioselective hydroxylation of steroid ketones 12-14 have been achieved at the C-17, C-16, C-3, and C-5 positions.
Persistent Identifierhttp://hdl.handle.net/10722/70106
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorWong, MKen_HK
dc.contributor.authorChung, NWen_HK
dc.contributor.authorHe, Len_HK
dc.contributor.authorWang, XCen_HK
dc.contributor.authorYan, Zen_HK
dc.contributor.authorTang, YCen_HK
dc.contributor.authorYang, Den_HK
dc.date.accessioned2010-09-06T06:19:46Z-
dc.date.available2010-09-06T06:19:46Z-
dc.date.issued2003en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2003, v. 68 n. 16, p. 6321-6328en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70106-
dc.description.abstractWe found that dioxiranes generated in situ from ketones 1-6 and Oxone underwent intramolecular oxidation of unactivated C-H bonds at δ sites of ketones to yield tetrahydropyrans. From the trans/cis ratio of oxidation products 1a and 2a as well as the retention of the configuration at the δ site of ketone 5, we proposed that the oxidation reaction proceeds through a concerted pathway under a spiro transition state. The intramolecular oxidation of ketone 6 showed the preference for a tertiary δ C-H bond over a secondary one. This intramolecular oxidation method can be extended to the oxidation of the tertiary γ′ C-H bond of ketones 9 and 10. For ketone 11 with two δ C-H bonds and one γ′ C-H bond linked respectively by a sp 3 hydrocarbon tether and a sp 2 ester tether, the oxidation took place exclusively at the δ C-H bonds. Finally, by introducing proper tethers, regioselective hydroxylation of steroid ketones 12-14 have been achieved at the C-17, C-16, C-3, and C-5 positions.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_HK
dc.relation.ispartofJournal of Organic Chemistryen_HK
dc.titleInvestigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in Situen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=68&spage=6321&epage=6328&date=2003&atitle=Investigation+on+the+regioselectivities+of+intramolecular+oxidation+of+unactivated+C-H+bonds+by+dioxiranes+generated+in+situen_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/jo0347011en_HK
dc.identifier.scopuseid_2-s2.0-0043032782en_HK
dc.identifier.hkuros91329en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0043032782&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume68en_HK
dc.identifier.issue16en_HK
dc.identifier.spage6321en_HK
dc.identifier.epage6328en_HK
dc.identifier.isiWOS:000184552500034-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridWong, MK=7403908449en_HK
dc.identifier.scopusauthoridChung, NW=8759035900en_HK
dc.identifier.scopusauthoridHe, L=55074306200en_HK
dc.identifier.scopusauthoridWang, XC=9744761800en_HK
dc.identifier.scopusauthoridYan, Z=7402519416en_HK
dc.identifier.scopusauthoridTang, YC=7404592447en_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats