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PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE HYDROXYMETHYLATED COMPOUNDS AND CATALYST THEREFOR

Foreign code F070001552
File No. E07612WO
Posted date Apr 6, 2007
Country WIPO
International application number 2006JP301293
International publication number WO 2006/080425
Date of international filing Jan 27, 2006
Date of international publication Aug 3, 2006
Priority data
  • P2005-022643 (Jan 31, 2005) JP
Title PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE HYDROXYMETHYLATED COMPOUNDS AND CATALYST THEREFOR
Abstract [PROBLEMS] To provide a process for producing optically active hydroxymethylated compoundsin high yields at high stereoselectivity with broad substrate generality, anda catalyst for the production. [MEANS FOR SOLVING PROBLEMS] The process comprises reactinga silicon enolate represented by the general formula (1) with formaldehyde ineither an aqueous solution or a mixed solvent of water and an organic solvent inthe presence of a catalyst obtained by mixing a ligand consisting of a chiral bipyridineor an antipode thereof with Bi(OTf)3: (1) wherein R5 to R7are each hydrogen, an aliphatic hydrocarbon group, an aliphatic mono- or poly-cyclichydrocarbon group, a mono- or poly-cyclic aromatic or araliphatic hydrocarbongroup, or a heterocyclic group with the proviso that R5 and R7are different from each other and R6 is not hydrogen; and R8'smay be the same or different and are each methyl, ethyl, or isopropyl.
Scope of claims (In Japanese)
【請求項1】水溶液中又は水と有機溶媒との混合溶媒中で、キラルなビピリジン化合物からなる配位子又はその対称体と、BiY3で表されるルイス酸(式中、Yはハロゲン原子、OAc、OCOCF3、ClO4、SbF6、PF6又はOSO2CF3を表す。)とを混合させて得られる触媒の存在下で、下式(式1)【化1】(式中、R5~R7は水素原子、脂肪族、炭化水素基、単環又は多環の脂環式炭化水素基、単環又は多環の芳香族もしくは芳香脂族炭化水素基、あるいは複素環基を表し、R5とR7はそれぞれ異なり、R6は水素原子以外であり、R8は、それぞれ同じであっても異なってもよく、メチル基、エチル基、又はイソプロピル基を表す)で表されるケイ素エノラートとホルムアルデヒドとを反応させることを含む、光学活性ヒドロキシメチル化化合物の製法。

【請求項2】前記キラルなビピリジン化合物からなる配位子は、下式(化2)【化2】(式中、R1は炭素数4以下のアルキル基またはフェニル基を表す)で表される請求項1に記載の製法。

【請求項3】(前記キラルなビピリジン化合物からなる配位子又はその対称体/前記ルイス酸)で表されるモル比を2.5以上とする請求項1又は2に記載の製法。

【請求項4】さらに2,2'-ビピリジンを添加剤として加える請求項1ないし3のいずれかに記載の製法。

【請求項5】キラルなビピリジン化合物からなる配位子又はその対称体と、Bi(OTf)3とを混合させて得られる触媒。
  • Applicant
  • ※All designated countries except for US in the data before July 2012
  • Japan Science And Technology Agency
  • Inventor
  • Kobayashi, Shu
  • Manabe, Kei
IPC(International Patent Classification)
Reference ( R and D project ) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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