CA1265536A - Production of optically pure organoboranes - Google Patents

Production of optically pure organoboranes

Info

Publication number
CA1265536A
CA1265536A CA000499696A CA499696A CA1265536A CA 1265536 A CA1265536 A CA 1265536A CA 000499696 A CA000499696 A CA 000499696A CA 499696 A CA499696 A CA 499696A CA 1265536 A CA1265536 A CA 1265536A
Authority
CA
Canada
Prior art keywords
solid
borane
alkene
converted
essentially
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
CA000499696A
Other languages
English (en)
French (fr)
Inventor
Herbert C. Brown
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aldrich Chemical Co Inc
Original Assignee
Aldrich Boranes Inc
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 Aldrich Boranes Inc filed Critical Aldrich Boranes Inc
Application granted granted Critical
Publication of CA1265536A publication Critical patent/CA1265536A/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/06—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
    • C07C35/28—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing seven carbon atoms
    • C07C35/29—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing seven carbon atoms being a (2.2.1) system
    • C07C35/30—Borneol; Isoborneol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • 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
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • 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
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA000499696A 1985-01-16 1986-01-16 Production of optically pure organoboranes Expired - Fee Related CA1265536A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/692,046 US4713380A (en) 1985-01-16 1985-01-16 Production of optically pure organoboranes
US692,046 1985-01-16

Publications (1)

Publication Number Publication Date
CA1265536A true CA1265536A (en) 1990-02-06

Family

ID=24779045

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000499696A Expired - Fee Related CA1265536A (en) 1985-01-16 1986-01-16 Production of optically pure organoboranes

Country Status (6)

Country Link
US (1) US4713380A (enExample)
EP (1) EP0188235B1 (enExample)
JP (1) JPS61210089A (enExample)
AT (1) ATE70275T1 (enExample)
CA (1) CA1265536A (enExample)
DE (1) DE3682783D1 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5043479A (en) * 1986-08-29 1991-08-27 Aldrich Chemical Company, Inc. Chemically and optically pure diisopinocampheylhaloboranes
US4906755A (en) * 1986-11-03 1990-03-06 Merrell Dow Pharmaceuticals Inc. Esters of hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3-(4H)-one and related compounds
DE3842554A1 (de) * 1988-12-17 1990-06-21 Bayer Ag Chirale verbindungen vom ss-binaphthyltyp, deren herstellung und deren verwendung
US4978794A (en) * 1990-03-26 1990-12-18 Aldrich Chemical Company, Inc. Novel β-(2-alkenyl)bis(2-isocaranyl)boranes
US5103063A (en) * 1990-08-03 1992-04-07 Aldrich Chemical Company, Inc. Intermediates useful for the chiral isoprenylation of aldehydes
US5220072A (en) * 1991-07-15 1993-06-15 Aldrich Chemical Co., Inc. Process of synthesizing chemically and optically pure B-halodiiso-2-ethylapopinocampheylboranes
WO2006125550A1 (de) * 2005-05-25 2006-11-30 Merck Patent Gmbh Verfahren zur herstellung von tetrahydropyranen aus tetrahydropyran-3-onen
WO2014121008A1 (en) * 2013-01-31 2014-08-07 Promerus, Llc Norbornenylhydrocarbylene dihydrocarbylboranes and methods of making the same
CN113024588A (zh) * 2021-03-22 2021-06-25 成都诺和晟泰生物科技有限公司 一种手性N-Boc-吡咯烷-3-硼酸类化合物的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3254129A (en) * 1961-01-17 1966-05-31 Herbert C Brown Optically active organoboranes
US3337643A (en) * 1963-10-17 1967-08-22 Colgate Palmolive Co Process for preparing optically active menthol
US3358034A (en) * 1964-03-12 1967-12-12 Herbert C Brown Selective hydroboration process
US4082810A (en) * 1971-02-09 1978-04-04 Aldrich-Boranes, Inc. Bulky trialkylborohydrides

Also Published As

Publication number Publication date
ATE70275T1 (de) 1991-12-15
DE3682783D1 (de) 1992-01-23
JPH0471916B2 (enExample) 1992-11-16
EP0188235B1 (en) 1991-12-11
EP0188235A3 (en) 1988-06-01
JPS61210089A (ja) 1986-09-18
US4713380A (en) 1987-12-15
EP0188235A2 (en) 1986-07-23

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