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N-Acyl-2-benzoxazolinones in titanium-mediated aldol reactions

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Title: N-Acyl-2-benzoxazolinones in titanium-mediated aldol reactions
Authors: Burlingame, Mark A. burlingame@kosan.com, Mendoza, Esteban1, Ashley, Gary W.1
Source: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Mar2004, Vol. 45 Issue 14, p2961. 4p.
Subjects: Titanium compounds, Aldehydes, Esters, Aldol condensation
Abstract: N-Acyl-2-benzoxazolinones readily form trichlorotitanium enolates that react rapidly with aldehydes to provide crystalline syn-aldol adducts in high yield. The resulting products are simply converted to amides, esters, and thioesters. A simple, economical synthesis of 3-hydroxy-2-methylpentanoate N-propionylcysteamine thioesters based on these findings is presented. [Copyright &y& Elsevier]
Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 12500579
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
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  Data: N-Acyl-2-benzoxazolinones in titanium-mediated aldol reactions
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  Data: <searchLink fieldCode="AR" term="%22Burlingame%2C+Mark+A%2E%22">Burlingame, Mark A.</searchLink><i> burlingame@kosan.com</i><br /><searchLink fieldCode="AR" term="%22Mendoza%2C+Esteban%22">Mendoza, Esteban</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Ashley%2C+Gary+W%2E%22">Ashley, Gary W.</searchLink><relatesTo>1</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Tetrahedron+Letters%3A+International+Organ+for+the+Rapid+Publication+of+Preliminary+Communications+in+Organic+Chemistry%22">Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry</searchLink>. Mar2004, Vol. 45 Issue 14, p2961. 4p.
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  Data: <searchLink fieldCode="DE" term="%22Titanium+compounds%22">Titanium compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Aldehydes%22">Aldehydes</searchLink><br /><searchLink fieldCode="DE" term="%22Esters%22">Esters</searchLink><br /><searchLink fieldCode="DE" term="%22Aldol+condensation%22">Aldol condensation</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: N-Acyl-2-benzoxazolinones readily form trichlorotitanium enolates that react rapidly with aldehydes to provide crystalline syn-aldol adducts in high yield. The resulting products are simply converted to amides, esters, and thioesters. A simple, economical synthesis of 3-hydroxy-2-methylpentanoate N-propionylcysteamine thioesters based on these findings is presented. [Copyright &y& Elsevier]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.tetlet.2004.02.029
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      – SubjectFull: Esters
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              Text: Mar2004
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