Kinetic Resolution of β-Substituted Olefinic Carboxylic Acids by Asymmetric Bromolactonization

被引：43

作者：

Murai, Kenichi ^{[1
]}

Matsushita, Tomoyo ^{[1
]}

Nakamura, Akira ^{[1
]}

Hyogo, Norimichi ^{[1
]}

Nakajima, Junki ^{[1
]}

Fujioka, Hiromichi ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 10期

关键词：

NONSTEROIDAL ANTIINFLAMMATORY DRUGS; ALPHA-ARYLALKANOIC ACIDS; ENANTIOSELECTIVE BROMOLACTONIZATION; ACHIRAL ALCOHOLS; ANHYDRIDES;

D O I：

10.1021/ol401007u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategically novel kinetic resolution of beta-substituted olefinic carboxylic acids is developed by asymmetric bromolactonization using an organocatalyst, 4-tBuPh-tris 1b. The cyclization stage, which provides delta-lactone, is proposed to be operative for discrimination of each enantiomer of carboxylic acids.

引用

下载

页码：2526 / 2529

页数：4

共 50 条

[31] KINETIC RESOLUTION OF RACEMIC CARBOXYLIC-ACIDS AND ALCOHOLS WITH HOMOCHIRAL ALCOHOLS AND CARBOXYLIC-ACIDS, RESPECTIVELY, AND THE MUKAIYAMA OR PALOMO REAGENTS
MAZON, A
NAJERA, C
YUS, M
HEUMANN, A
TETRAHEDRON-ASYMMETRY, 1992, 3 (11) : 1455 - 1466
[32] Applications of chiral naphthyloxycyclohexanols in deracemization of α-substituted carboxylic acids by dynamic thermodynamic resolution
Khanvilkar, Aditya N.
Samanta, Sudeep G.
Bedekar, Ashutosh V.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (10) : 2670 - 2683
[33] Development of Kinetic Resolution of Racemic Alcohols and Carboxylic Acids Accompanied with Dehydration Condensation
Shiina, Isamu
Nakata, Kenya
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2014, 72 (08) : 919 - 928
[34] 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
[35] 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
[36] Kinetic resolution of racemic α-hydroxyphosphonates by asymmetric esterification using achiral carboxylic acids with pivalic anhydride and a chiral acyl-transfer catalyst
Shiina, Isamu
Ono, Keisuke
Nakahara, Takayoshi
CHEMICAL COMMUNICATIONS, 2013, 49 (91) : 10700 - 10702
[37] Enantioselective Bromolactonization of Deactivated Olefinic Acids: Studies Toward the Synthesis of Brominated Isochroman-1,4-diones
Li, Danqing
He, Hailong
Huang, Xiaodan
Yu, Pei
Jiang, Xiaojian
SYNOPEN, 2018, 2 (04): : 293 - 297
[38] A reactivity/affinity switch for parallel kinetic resolution:: α-amino acid quasienantiomers and the resolution of cyclopropene carboxylic acids
Liao, LA
Zhang, F
Dmitrenko, O
Bach, RD
Fox, JM
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) : 4490 - 4491
[39] Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination
Yu, Shaoze
Bao, Hanyang
Zhang, Dekun
Yang, Xiaoyu
NATURE COMMUNICATIONS, 2023, 14 (01)
[40] Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst
Tan, Chong Kiat
Le, Chencheng
Yeung, Ying-Yeung
CHEMICAL COMMUNICATIONS, 2012, 48 (46) : 5793 - 5795

← 1 2 3 4 5 →