Title:
PRODUCTION METHOD FOR 1,1'-BINAPHTHYL DERIVATIVE, AND 1,1'-BINAPHTHYL DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2017/145716
Kind Code:
A1
Abstract:
In this production method according to the present disclosure, a 1,1'-binaphthyl derivative precursor having, at each of the 2-position and 2'-position of a 1,1'-binaphthyl skeleton, an electron-donating group including an oxygen atom directly bonded to the skeleton; an organic acid; and an iodinating agent or a brominating agent are mixed together. The production method according to the present disclosure allows obtaining of a 1,1'-binaphthyl derivative in which a substituent is introduced into the 8-position and/or 8'-position of the 1,1'-binaphthyl skeleton. The 1,1'-binaphthyl derivative obtained by the production method according to the present disclosure can be a compound in which a substituent is further introduced into at least one position selected from among the 4-position, 4'-position, 5-position, 5'-position, 6-position, and 6'-position of the 1,1'-binaphthyl skeleton.
Inventors:
SHIMADA TOYOSHI (JP)
NAKANISHI KAZUKI (JP)
NAKANISHI KAZUKI (JP)
Application Number:
PCT/JP2017/004117
Publication Date:
August 31, 2017
Filing Date:
February 03, 2017
Export Citation:
Assignee:
UNIV KYOTO (JP)
International Classes:
C07C303/26; C07C46/02; C07C50/32; C07C309/65; C07C309/66
Domestic Patent References:
| WO2011111762A1 | 2011-09-15 |
Other References:
TSUBAKI,K. ET AL.: "Synthesis of chiral 2,2'- dimethyl-1,1'-binaphthyl-8,8'-diamine and barriers of atropisomerization of the related binaphthyls", TETRAHEDRON : ASYMMETRY, vol. 18, no. 8, 2007, pages 1017 - 1021, XP022088358
KOLOTUCHIN,S.V. ET AL.: "Synthesis of 8,8'- disubstituted 1,1'-binaphthyls stable to atropisomerization: 2,2'-dimethyl-1,1'- binaphthalene-8,8'-diol and 2,2'-dimethyl-8,8'- bis(4-tert-butyloxazolyl)-1,1'-binaphthyl", JOURNAL OF ORGANIC CHEMISTRY, vol. 64, no. 21, 1999, pages 7921 - 7928, XP055411811
YUDIN,A.K. ET AL.: "F8BINOL, an Electronically Perturbed Version of BINOL with Remarkable Configurational Stability", ORGANIC LETTERS, vol. 2, no. 1, 2000, pages 41 - 44, XP002172603
CHEN,Y. ET AL.: "Regioselective Substitution of Fluorine in F8BINOL as a Versatile Route to New Ligands with Axial Chirality", ORGANIC LETTERS, vol. 2, no. 22, 2000, pages 3433 - 3436, XP055411821
MARTYN,L.J. ET AL.: "Catalytic applications of F8BINOL: asymmetric oxidation of sulfides to sulfoxides", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 603, no. 1, 2000, pages 98 - 104, XP004213443
YEKTA,S. ET AL.: "Preparation and catalytic applications of partially fluorinated binaphthol ligands", JOURNAL OF FLUORINE CHEMISTRY, vol. 125, no. 4, 2004, pages 517 - 525, XP004507052
BILAND-THOMMEN,A.S. ET AL.: "Double benzyne-furan cycloaddition and the assembly of 1,1'- binaphthyl and 1,1'-dinaphthyl ether systems", TETRAHEDRON LETTERS, vol. 45, no. 16, 2004, pages 3181 - 3184, XP004498974
LAATSCH,H.: "Dimeric naphthoquinones. XVI. Synthesis of maritinone and other 8,8'- bijuglones", LIEBIGS ANNALEN DER CHEMIE, vol. 12, 1985, pages 2420 - 42, XP055411828
KAMEI,T. ET AL.: "Scandium triflate-catalyzed 6,6'-diiodination of 2,2'-dimethoxy-1,1'- binaphthyl with 1,3-diiodo-5,5- dimethylhydantoin", TETRAHEDRON LETTERS, vol. 53, no. 30, 2012, pages 3894 - 3896, XP028496026
KOLOTUCHIN,S.V. ET AL.: "Synthesis of 8,8'- disubstituted 1,1'-binaphthyls stable to atropisomerization: 2,2'-dimethyl-1,1'- binaphthalene-8,8'-diol and 2,2'-dimethyl-8,8'- bis(4-tert-butyloxazolyl)-1,1'-binaphthyl", JOURNAL OF ORGANIC CHEMISTRY, vol. 64, no. 21, 1999, pages 7921 - 7928, XP055411811
YUDIN,A.K. ET AL.: "F8BINOL, an Electronically Perturbed Version of BINOL with Remarkable Configurational Stability", ORGANIC LETTERS, vol. 2, no. 1, 2000, pages 41 - 44, XP002172603
CHEN,Y. ET AL.: "Regioselective Substitution of Fluorine in F8BINOL as a Versatile Route to New Ligands with Axial Chirality", ORGANIC LETTERS, vol. 2, no. 22, 2000, pages 3433 - 3436, XP055411821
MARTYN,L.J. ET AL.: "Catalytic applications of F8BINOL: asymmetric oxidation of sulfides to sulfoxides", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 603, no. 1, 2000, pages 98 - 104, XP004213443
YEKTA,S. ET AL.: "Preparation and catalytic applications of partially fluorinated binaphthol ligands", JOURNAL OF FLUORINE CHEMISTRY, vol. 125, no. 4, 2004, pages 517 - 525, XP004507052
BILAND-THOMMEN,A.S. ET AL.: "Double benzyne-furan cycloaddition and the assembly of 1,1'- binaphthyl and 1,1'-dinaphthyl ether systems", TETRAHEDRON LETTERS, vol. 45, no. 16, 2004, pages 3181 - 3184, XP004498974
LAATSCH,H.: "Dimeric naphthoquinones. XVI. Synthesis of maritinone and other 8,8'- bijuglones", LIEBIGS ANNALEN DER CHEMIE, vol. 12, 1985, pages 2420 - 42, XP055411828
KAMEI,T. ET AL.: "Scandium triflate-catalyzed 6,6'-diiodination of 2,2'-dimethoxy-1,1'- binaphthyl with 1,3-diiodo-5,5- dimethylhydantoin", TETRAHEDRON LETTERS, vol. 53, no. 30, 2012, pages 3894 - 3896, XP028496026
Attorney, Agent or Firm:
KAMADA Koichi (JP)
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