Title:
PROCESS FOR PRODUCING ALCOHOL ANALOGUE
Document Type and Number:
WIPO Patent Application WO/2016/047388
Kind Code:
A1
Abstract:
Provided is a process for producing an optically active hydroxyaldehyde or aminohydroxyaldehyde.
The process for producing an optically active hydroxyaldehyde or aminohydroxyaldehyde is characterized by reacting an aldehyde or an imine with a boric acid enol ester in the presence of a copper compound and an optically active bidentate phosphine compound.
Inventors:
KANAI MOTOMU (JP)
MATSUNAGA SHIGEKI (JP)
MATSUNAGA SHIGEKI (JP)
Application Number:
PCT/JP2015/074733
Publication Date:
March 31, 2016
Filing Date:
August 31, 2015
Export Citation:
Assignee:
TAKASAGO PERFUMERY CO LTD (JP)
International Classes:
C07C45/00; C07C47/19; C07C47/192; C07C47/27; C07C47/273; C07F5/04; C07F9/36; C07B53/00; C07B61/00
Other References:
HOFFMANN,R.W. ET AL.: "Syn-selective addition of enol borates to aldehydes", TETRAHEDRON LETTERS, vol. 25, no. 17, 1984, pages 1781 - 4, XP055422765, ISSN: 0040-4039
GENNARI,C. ET AL.: "Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: mechanistic and stereochemical details", TETRAHEDRON, vol. 40, no. 20, 1984, pages 4051 - 8, XP055422768, ISSN: 0040-4020
GENNARI,C. ET AL.: "Enol boronates: new practical reagents for regioselective aldol condensations", TETRAHEDRON LETTERS, vol. 25, no. 21, 1984, pages 2279 - 82, XP055422779, ISSN: 0040-4039
GENNARI,C. ET AL.: "Stereoselective aldol condensations via enol boronates", TETRAHEDRON LETTERS, vol. 25, no. 21, 1984, pages 2283 - 6, XP055423081, ISSN: 0040-4039
HOFFMANN,R.W. ET AL.: "Stereoselective syntheses of alcohols, XXV. Generation of enol borates and their addition to aldehydes", LIEBIGS ANNALEN DER CHEMIE, no. 11, 1987, pages 977 - 85, XP055423090, ISSN: 0170-2041
MUKAIYAMA,T. ET AL.: "Stereoselective crossed aldol reaction via boron enolates generated from a-iodo ketones and 9-borabicyclo[3.3.1] nonane", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 76, no. 4, 2003, pages 813 - 823, XP009501432, ISSN: 0009-2673
OISAKI KOUNOSUKE ET AL.: "New chiral bis(diphenylphospholane) ligands: design, synthesis, and application to catalytic enantioselective aldol reaction to ketones", TETRAHEDRON LETTERS, vol. 46, no. 25, 2005, pages 4325 - 9, XP027863912, ISSN: 0040-4039
FERRARIS,D. ET AL.: "Catalytic, enantioselective alkylations of N,O- and N, N-acetals and hemiacetals", TETRAHEDRON, vol. 55, no. 29, 1999, pages 8869 - 8882, XP004171392, ISSN: 0040-4020, DOI: doi:10.1016/S0040-4020(99)00450-0
OHKOUCHI, M. ET AL.: "Efficient Mukaiyama Aldol Reaction by Silver(I) Carboxylate-Bis (phosphine) Catalysts", JOURNAL OF THE CHEMICAL SOCIETY OF JAPAN, no. 2, 2002, pages 223 - 229, XP055423116, ISSN: 0369-4577
LU ,A. ET AL.: "Chiral N-thiophosphoryl imine- induced diastereoselective aza-Morita-Baylis- Hillman reaction", TETRAHEDRON : ASYMMETRY, vol. 19, no. 16, 2008, pages 1886 - 1890, XP025347787, ISSN: 0957-4166, DOI: doi:10.1016/j.tetasy.2008.08.010
GENNARI,C. ET AL.: "Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: mechanistic and stereochemical details", TETRAHEDRON, vol. 40, no. 20, 1984, pages 4051 - 8, XP055422768, ISSN: 0040-4020
GENNARI,C. ET AL.: "Enol boronates: new practical reagents for regioselective aldol condensations", TETRAHEDRON LETTERS, vol. 25, no. 21, 1984, pages 2279 - 82, XP055422779, ISSN: 0040-4039
GENNARI,C. ET AL.: "Stereoselective aldol condensations via enol boronates", TETRAHEDRON LETTERS, vol. 25, no. 21, 1984, pages 2283 - 6, XP055423081, ISSN: 0040-4039
HOFFMANN,R.W. ET AL.: "Stereoselective syntheses of alcohols, XXV. Generation of enol borates and their addition to aldehydes", LIEBIGS ANNALEN DER CHEMIE, no. 11, 1987, pages 977 - 85, XP055423090, ISSN: 0170-2041
MUKAIYAMA,T. ET AL.: "Stereoselective crossed aldol reaction via boron enolates generated from a-iodo ketones and 9-borabicyclo[3.3.1] nonane", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 76, no. 4, 2003, pages 813 - 823, XP009501432, ISSN: 0009-2673
OISAKI KOUNOSUKE ET AL.: "New chiral bis(diphenylphospholane) ligands: design, synthesis, and application to catalytic enantioselective aldol reaction to ketones", TETRAHEDRON LETTERS, vol. 46, no. 25, 2005, pages 4325 - 9, XP027863912, ISSN: 0040-4039
FERRARIS,D. ET AL.: "Catalytic, enantioselective alkylations of N,O- and N, N-acetals and hemiacetals", TETRAHEDRON, vol. 55, no. 29, 1999, pages 8869 - 8882, XP004171392, ISSN: 0040-4020, DOI: doi:10.1016/S0040-4020(99)00450-0
OHKOUCHI, M. ET AL.: "Efficient Mukaiyama Aldol Reaction by Silver(I) Carboxylate-Bis (phosphine) Catalysts", JOURNAL OF THE CHEMICAL SOCIETY OF JAPAN, no. 2, 2002, pages 223 - 229, XP055423116, ISSN: 0369-4577
LU ,A. ET AL.: "Chiral N-thiophosphoryl imine- induced diastereoselective aza-Morita-Baylis- Hillman reaction", TETRAHEDRON : ASYMMETRY, vol. 19, no. 16, 2008, pages 1886 - 1890, XP025347787, ISSN: 0957-4166, DOI: doi:10.1016/j.tetasy.2008.08.010
Attorney, Agent or Firm:
SAEKI, Norio et al. (JP)
Norio Saeki (JP)
Norio Saeki (JP)
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