Kinetic resolution of racemic α-hydroxyphosphonates by asymmetric esterification using achiral carboxylic acids with pivalic anhydride and a chiral acyl-transfer catalyst

被引：26

作者：

Shiina, Isamu ^{[1
]}

Ono, Keisuke ^{[1
]}

Nakahara, Takayoshi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 91期

关键词：

ALCOHOLS; INHIBITORS; HYDROXYALKANEPHOSPHONATES; ANALOGS; PHOSPHONATES;

D O I：

10.1039/c3cc44293d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical protocol is developed to directly provide chiral alpha-acyloxyphosphonates and alpha-hydroxyphosphonates from (+/-)-alpha-hydroxyphosphonates utilizing the transacylation process to generate the mixed anhydrides from acid components and pivalic anhydride in the presence of organocatalysts (s-value = 33-518).

引用

页码：10700 / 10702

页数：3

共 48 条

[1] Kinetic Resolution of Racemic 1-Heteroarylalkanols by Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-transfer Catalyst
Shiina, Isamu
Ono, Keisuke
Nakata, Kenya
CHEMISTRY LETTERS, 2011, 40 (02) : 147 - 149
[2] Kinetic Resolution of Racemic 2-Hydroxy-γ-butyrolactones by Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst
Nakata, Kenya
Gotoh, Kouya
Ono, Keisuke
Futami, Kengo
Shiina, Isamu
ORGANIC LETTERS, 2013, 15 (06) : 1170 - 1173
[3] Kinetic Resolution of Racemic α-Arylalkanoic Acids with Achiral Alcohols via the Asymmetric Esterification Using Carboxylic Anhydrides and Acyl-Transfer Catalysts
Shiina, Isamu
Nakata, Kenya
Ono, Keisuke
Onda, Yu-suke
Itagak, Makoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) : 11629 - 11641
[4] Kinetic Resolution of the Racemic 2-Hydroxyalkanoates Using the Enantioselective Mixed-Anhydride Method with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst
Shiina, Isamu
Nakata, Kenya
Ono, Keisuke
Sugimoto, Masuhiro
Sekiguchi, Akihiro
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) : 167 - 172
[5] An effective kinetic resolution of racemic α-arylpropanoic acids, α-arylbutanoic acids, and β-substituted-α-arylpropanoic acids with bis(9-phenanthryl)methanol as a new achiral nucleophile in the asymmetric esterification using carboxylic anhydrides and the acyl-transfer catalyst
Nakata, Kenya
Onda, Yu-suke
Ono, Keisuke
Shiina, Isamu
TETRAHEDRON LETTERS, 2010, 51 (43) : 5666 - 5669
[6] A convenient method for the kinetic resolution of racemic 2-hydroxyalkanoates using diphenylacetic anhydride (DPHAA) and a chiral acyl-transfer catalyst
Nakata, Kenya
Sekiguchi, Akihiro
Shiina, Isamu
TETRAHEDRON-ASYMMETRY, 2011, 22 (16-17) : 1610 - 1619
[7] Kinetic Resolution of Racemic Secondary Benzylic Alcohols by the Enantioselective Esterification Using Pyridine-3-carboxylic Anhydride (3-PCA) with Chiral Acyl-Transfer Catalysts
Shiina, Isamu
Nakata, Kenya
Ono, Keisuke
Mukaiyama, Teruaki
HELVETICA CHIMICA ACTA, 2012, 95 (10) : 1891 - 1911
[8] Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst
Murata, Takatsugu
Kawanishi, Tatsuya
Sekiguchi, Akihiro
Ishikawa, Ryo
Ono, Keisuke
Nakata, Kenya
Shiina, Isamu
MOLECULES, 2018, 23 (08)
[9] AN EFFECTIVE KINETIC RESOLUTION OF RACEMIC SECONDARY BENZYLIC ALCOHOLS USING 3-PYRIDINECARBOXYLIC ANHYDRIDE AND A CHIRAL ACYL-TRANSFER CATALYST IN THE ABSENCE OF TERTIARY AMINE
Nakata, Kenya
Shiina, Isamu
HETEROCYCLES, 2010, 80 (01) : 169 - 175
[10] KINETIC RESOLUTION OF RACEMIC 2-HYDROXYACETALS BY ASYMMETRIC ESTERIFICATION USING A MIXED ANHYDRIDE PROTOCOL
Nakata, Kenya
Tokumaru, Eri
Saitoh, Takahiro
Nakahara, Takayoshi
Ono, Keisuke
Murata, Takatsugu
Shiina, Isamu
HETEROCYCLES, 2017, 95 (01) : 277 - 289

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