公开(公告)号：EP1724251B1

公开(公告)日：2015-09-16

申请号：EP05704190.7

申请日：2005-01-27

Applicant: Japan Science and Technology Agency

Inventor： KOBAYASHI, Shu ,  MANABE, Kei

IPC: C07C45/00 ,  B01J31/14 ,  C07C45/75 ,  C07C49/497 ,  C07C49/733 ,  C07C49/82 ,  C07C327/22

CPC classification number: C07C327/22 ,  C07B53/00 ,  C07C45/512 ,  C07C2601/08 ,  C07C2601/14 ,  C07C2601/18 ,  C07C2602/08 ,  C07C2602/10 ,  C07C49/747 ,  C07C49/82 ,  C07C49/717 ,  C07C49/713 ,  C07C49/707 ,  C07C49/248

公开(公告)号：EP1852412B1

公开(公告)日：2011-03-16

申请号：EP06712459.4

申请日：2006-01-27

Applicant: Japan Science and Technology Agency

Inventor： KOBAYASHI, Shu ,  MANABE, Kei

IPC: C07C45/75 ,  B01J31/22 ,  C07B53/00 ,  C07C49/497 ,  C07C49/513 ,  C07C49/82 ,  C07B61/00

CPC classification number: B01J31/2213 ,  B01J31/1815 ,  B01J2231/321 ,  B01J2531/0252 ,  B01J2531/54 ,  C07B53/00 ,  C07B2200/07 ,  C07C45/511 ,  C07C49/497 ,  C07C49/747 ,  C07C49/82 ,  C07C49/84

Abstract: [PROBLEMS] To provide a process for producing optically active hydroxymethylated compounds in high yields at high stereoselectivity with broad substrate generality, and a catalyst for the production. [MEANS FOR SOLVING PROBLEMS] The process comprises reacting a silicon enolate represented by the general formula (1) with formaldehyde in either an aqueous solution or a mixed solvent of water and an organic solvent in the presence of a catalyst obtained by mixing a ligand consisting of a chiral bipyridine or an antipode thereof with Bi(OTf)3: (1) wherein R5 to R7 are each hydrogen, an aliphatic hydrocarbon group, an aliphatic mono- or poly-cyclic hydrocarbon group, a mono- or poly-cyclic aromatic or araliphatic hydrocarbon group, or a heterocyclic group with the proviso that R5 and R7 are different from each other and R6 is not hydrogen; and R8's may be the same or different and are each methyl, ethyl, or isopropyl.

公开(公告)号：EP1375464B1

公开(公告)日：2009-03-04

申请号：EP02703945.2

申请日：2002-03-08

Applicant: Japan Science and Technology Agency

Inventor： KOBAYASHI, Shu ,  MANABE, Kei

IPC: C07C45/70 ,  C07C45/72 ,  C07C49/83 ,  C07B61/00

CPC classification number: C07C45/511

Abstract: A method for an aldol reaction in water, characterized in that an aldehyde and an silyl enol ether is reacted in water as a medium in the presence of a boronic acid represented by the general formula (1): R R BOH (1) wherein R and R are hydrocarbon groups which may be the same or different and may have a substituent, a surfactant and a Brfnsted acid. The method for an aldol reaction in water allows the production of a product with high selectivity in high yield by the use of a boron source in an catalytic amount.

公开(公告)号：EP1852412A1

公开(公告)日：2007-11-07

申请号：EP06712459.4

申请日：2006-01-27

Applicant: Japan Science and Technology Agency

Inventor： KOBAYASHI, Shu ,  MANABE, Kei

IPC: C07C45/75 ,  B01J31/22 ,  C07B53/00 ,  C07C49/497 ,  C07C49/513 ,  C07C49/82 ,  C07B61/00

CPC classification number: B01J31/2213 ,  B01J31/1815 ,  B01J2231/321 ,  B01J2531/0252 ,  B01J2531/54 ,  C07B53/00 ,  C07B2200/07 ,  C07C45/511 ,  C07C49/497 ,  C07C49/747 ,  C07C49/82 ,  C07C49/84

Abstract: A silicon enolate represented by the following formula (Formula 1)

(in the formula, R 5 to R 7 represent hydrogen atoms, aliphatic hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, monocyclic or polycyclic aromatic or aromatic-aliphatic hydrocarbon groups or heterocyclic groups, R 5 and R 7 are different, R 6 is not a hydrogen atom, each R 8 may be identical or different and represents a methyl group, ethyl group or isopropyl group) and formaldehyde are allowed to react in an aqueous solution or a mixed solvent of water and an organic solvent in the presence of a catalyst obtained by mixing a ligand comprising a chiral bipyridine compound or its antipode and Bi(OTf) 3 .

Abstract translation: 由下式（式1）（式中，R 5〜R 7表示的硅烯醇表示氢原子，脂族烃基，单环或多环脂环族烃基，单环或多环芳族或芳族 - 脂族烃基或杂环基团 中，R 5和R 7是不同的，R 6不是氢原子，各R 8可以相同或不同，并且darstellt甲基，乙基或异丙基）和甲醛被允许在水溶液或混合反应 溶剂的水和有机溶剂中通过混合的配位体，包括手性联吡啶化合物或与其对映体和Bi（OTF）获得的催化剂的存在下进行。3

公开(公告)号：EP1724251A1

公开(公告)日：2006-11-22

申请号：EP05704190.7

申请日：2005-01-27

Applicant: Japan Science and Technology Agency

Inventor： KOBAYASHI, Shu ,  MANABE, Kei

IPC: C07C45/00 ,  B01J31/14 ,  C07C45/75 ,  C07C49/497 ,  C07C49/733 ,  C07C49/82 ,  C07C327/22

CPC classification number: C07C327/22 ,  C07B53/00 ,  C07C45/512 ,  C07C2601/08 ,  C07C2601/14 ,  C07C2601/18 ,  C07C2602/08 ,  C07C2602/10 ,  C07C49/747 ,  C07C49/82 ,  C07C49/717 ,  C07C49/713 ,  C07C49/707 ,  C07C49/248

Abstract: The present invention presents a catalyst that allows asymmetric hydroxymethylation reactions to progress with excellent asymmetric selectivity and a production method for optically active hydroxymethylated compounds using the catalyst.
Optically active hydroxymethylated compounds are obtained with excellent asymmetric selectivity by using a catalyst obtained by mixing chiral ligands (for example, chemical formula 4)

with scandium triflate and the like.