课题基金 / 基金详情

Effective Enzymatic Kinetic Resolution of Alcohols using Reactive Ketene-acetal Acylating Reagents

Effective Enzymatic Kinetic Resolution of Alcohols using Reactive Ketene-acetal Acylating Reagents
使用反应性乙烯酮缩醛酰化试剂对醇进行有效的酶动力学拆分
批准号:
09557180
负责人:
KITA Yasuyuki
金额:
$4.16万
依托单位:
依托单位国家:
日本
项目类别:
Grant-in-Aid for Scientific Research (B)
财政年份:
1997
资助国家:
日本
项目状态:
已结题
起止时间:
1997 至 1998

项目摘要

项目成果

KITA Yasuyuki的其他基金

相关文献

中文摘要
翻译
点击翻译按钮获取中文摘要
英文摘要
In recent years, enzyme-catalyzed kinetic resolution of racemic alcohols using vinyl esters (VEs) has become one of the most commonly employed tools for asymmetric syntheses. However, in this method there remain some problems such as deactivation of enzymes by the by-product, viz., acetaldehyde and difficulties in the preparation of VEs having various acyl moieties. We have recently established a convenient method for preparation of ketene acetal acylating reagents [H2C=C(OEt)OCOR] (1) from the corresponding carboxylic acids [JCS 1, 1993]. We applied 1 to the enzymatic reactions for the first time and have disclosed an effective kinetic resolution method featuring similar to higher reactivity and selectivity than the previous methods as well as generation of a by-product, viz., ethyl acetate, which does not deactivate the enzymes [TL, 1996]. By the use of 1, this project aims at establishing practical kinetic resolution protocols and developing novel asymmetric synthetic method that co … More uld not be attained by the previous methods using VEs. The followings are summary of the results :1. We have disclosed versatile applicability of our new method to variety of secondaryalcohols. We have also developed one-pot performing method involving in situ preparation of I followed by the kinetic resolution, which enabled us to use 1 having labile acyl moiety that was difficult to isolate.2. Lipase-catalyzed asymmetrization of prochiral 2, 2-disubstituted 1, 3-propanediols was developed using the benzoate (1 ; R = Ph), giving high chemical and optical yields of the products bearing quaternary carbon centers. This protocol enabled us to accomplish an asymmetric synthesis of the quaternary carbon center of antitumor antibiotic, fredericamycin A, and thereby, great progress was made in our another project towards the asymmetric total synthesis of this natural product.3. A novel lipase-catalyzed tandem asymmetric synthesis has been developed, which involves in situ preparation of 1-ethoxyvinyl methyl fumarate (1 ; R=CH=CHCO_2Me), lipase-catalyzed kinetic resolution of (2-furyl) carbinols, and intramolecular Diels-Alder reaction of thus introduced acyl moiety, providing the tricyclic adducts with up to 99% ee. We also have discovered for the first time that this lipase can affect the Diels-Alder reaction to improve enantio-and diastereo-selectivities. Less
期刊论文(12)
专著(0)
科研奖励(0)
会议论文
Kita,Yasuyuki: "Studies of Asymmetric Total Synthesis of Antitumor Antibiotic,Fredericamycin A(Review)" 有機合成化学協会誌. 56. 963-974 (1998)
Kita,Yasuyuki:“抗肿瘤抗生素 Fredericamycin A 的不对称全合成研究(评论)”有机合成化学学会杂志 56. 963-974 (1998)。
DOI: --
发表时间:
期刊:
影响因子: --
作者: []
通讯作者:
Kita, Yasuyuki: "Asymmetric Diels-Alder Reaction Via Enzymatic Kinetic Resolution using Ethoxyvinyl Methyl Fumarate" Chem.Commun.1183-1184 (1998)
Kita, Yasuyuki:“使用乙氧基乙烯基富马酸甲酯通过酶促动力学拆分进行不对称狄尔斯-阿尔德反应”Chem.Commun.1183-1184 (1998)
DOI: --
发表时间:
期刊:
影响因子: --
作者: []
通讯作者:
北 泰行: "光学活性スピロ化合物の新構築 : 抗腫瘍活性天然物の全合成" ファルマシア. 34. 969-971 (1998)
Yasuyuki Kita:“旋光活性螺环化合物的新结构:抗肿瘤活性天然产物的全合成” Pharmacia 34. 969-971 (1998)。
DOI: --
发表时间:
期刊:
影响因子: --
作者: []
通讯作者:
Akai,Shuji: "Recent Progress in the Synthesis of p-Quinones and p-Dihydroquinones through Oxidation of Phenol Derivatives. A Review" Org.Prep.Proced.Int.30. 603-629 (1998)
Akai,Shuji:“通过苯酚衍生物氧化合成对醌和对二氢醌的最新进展。综述”Org.Prep.Proced.Int.30。
DOI: --
发表时间:
期刊:
影响因子: --
作者: []
通讯作者:
12
    Research on Development of Biologically Functional Molecules Aiming at DrugDiscovery: An Approach by Creative Organic Syntheses
    • 批准号:
      21249002
    • 项目类别:
      Grant-in-Aid for Scientific Research (A)
    • 资助金额:
      $23.46万
    • 财政年份:
      2009
    • 负责人:
      KITA Yasuyuki
    • 依托单位:
    Creative and Highly Efficient Synthesis of Biologically Functional Molecules and Its Application in Drug Development Study
    • 批准号:
      18209002
    • 项目类别:
      Grant-in-Aid for Scientific Research (A)
    • 资助金额:
      $27.46万
    • 财政年份:
      2006
    • 负责人:
      KITA Yasuyuki
    • 依托单位:
    Environmentally benign reactions for large-scale syntheses of bioactive natural products and their application to drug discovery
    • 批准号:
      13853010
    • 项目类别:
      Grant-in-Aid for Scientific Research (S)
    • 资助金额:
      $76.13万
    • 财政年份:
      2001
    • 负责人:
      KITA Yasuyuki
    • 依托单位:
    Development and Application of the Asymmetric Synthesis Using Reactive Acetals
    • 批准号:
      12470477
    • 项目类别:
      Grant-in-Aid for Scientific Research (B)
    • 资助金额:
      $8.83万
    • 财政年份:
      2000
    • 负责人:
      KITA Yasuyuki
    • 依托单位: