WO2009137691A3 - 1,3-diol synthesis via controlled, radical-mediated c-h functionalization - Google Patents

1,3-diol synthesis via controlled, radical-mediated c-h functionalization Download PDF

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Publication number
WO2009137691A3
WO2009137691A3 PCT/US2009/043163 US2009043163W WO2009137691A3 WO 2009137691 A3 WO2009137691 A3 WO 2009137691A3 US 2009043163 W US2009043163 W US 2009043163W WO 2009137691 A3 WO2009137691 A3 WO 2009137691A3
Authority
WO
WIPO (PCT)
Prior art keywords
functionalization
mediated
radical
via controlled
synthesis via
Prior art date
Application number
PCT/US2009/043163
Other languages
French (fr)
Other versions
WO2009137691A2 (en
Inventor
Ke Chen
Jeremy M. Richter
Phil S. Baran
Original Assignee
The Scripps Research Institute
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Scripps Research Institute filed Critical The Scripps Research Institute
Publication of WO2009137691A2 publication Critical patent/WO2009137691A2/en
Publication of WO2009137691A3 publication Critical patent/WO2009137691A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B41/00—Formation or introduction of functional groups containing oxygen
    • C07B41/02—Formation or introduction of functional groups containing oxygen of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
    • C07C2602/28—Hydrogenated naphthalenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The conversion of an alcohol into a 1,3- diol via controlled, radical-mediated C-H functionalization has been demonstrated. The method entails nearly quantitative conversion of an alcohol to the corresponding N-substitutedcarbamate, followed by a variant of the Hofffman-Lδffler-Freytag reaction, cyclization, and hydrolysis to provide a 1,3-diol.
PCT/US2009/043163 2008-05-09 2009-05-07 1,3-diol synthesis via controlled, radical-mediated c-h functionalization WO2009137691A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US5202708P 2008-05-09 2008-05-09
US61/052,027 2008-05-09
US5238908P 2008-05-12 2008-05-12
US61/052,389 2008-05-12

Publications (2)

Publication Number Publication Date
WO2009137691A2 WO2009137691A2 (en) 2009-11-12
WO2009137691A3 true WO2009137691A3 (en) 2009-12-23

Family

ID=41265408

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/043163 WO2009137691A2 (en) 2008-05-09 2009-05-07 1,3-diol synthesis via controlled, radical-mediated c-h functionalization

Country Status (1)

Country Link
WO (1) WO2009137691A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104803840B (en) * 2014-01-29 2016-08-17 中国科学院海洋研究所 Antibacterium monoterpene and its production and use

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4873379A (en) * 1988-05-25 1989-10-10 Hoechst Celanese Corporation Process for making 1,3-diols from epoxides
US20020161021A1 (en) * 1997-12-19 2002-10-31 Bosch Robert Lee Process for the synthesis of 1,3-diols
US6545190B2 (en) * 2001-03-15 2003-04-08 Shell Oil Company One step process for preparing a 1,3-diol
US6548716B1 (en) * 2000-03-22 2003-04-15 Shell Oil Company Process for preparing a 1,3-diol

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4873379A (en) * 1988-05-25 1989-10-10 Hoechst Celanese Corporation Process for making 1,3-diols from epoxides
US20020161021A1 (en) * 1997-12-19 2002-10-31 Bosch Robert Lee Process for the synthesis of 1,3-diols
US6548716B1 (en) * 2000-03-22 2003-04-15 Shell Oil Company Process for preparing a 1,3-diol
US6545190B2 (en) * 2001-03-15 2003-04-08 Shell Oil Company One step process for preparing a 1,3-diol

Also Published As

Publication number Publication date
WO2009137691A2 (en) 2009-11-12

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