Direct Catalytic Asymmetric Synthesis of β-Hydroxy Acids from Malonic Acid

被引：43

作者：

Gao, Hang ^{[1
]}

Luo, Zhenli ^{[1
]}

Ge, Pingjin ^{[1
]}

He, Junqian ^{[1
]}

Zhou, Feng ^{[1
]}

Zheng, Peipei ^{[1
]}

Jiang, Jun ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

基金：

中国国家自然科学基金;

关键词：

DECARBOXYLATIVE ALDOL REACTION; MANNICH-TYPE REACTIONS; CARBOXYLIC-ACIDS; HALF THIOESTERS; RICE BRAN; KETOACIDS; ORGANOCATALYSTS; CONSTRUCTION; CONDENSATION; TRYPTANTHRIN;

D O I：

10.1021/acs.orglett.5b02891

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nickel(II) catalyzed asymmetric synthesis of beta-hydroxy acids from malonic acid and ketones was developed, revealing for the first time the synthetic utility of malonic acid in the construction of chiral carboxyl acids; importantly, the synthetic potential of this strategy was further demonstrated by the rapid construction of cephalanthrin A, phaitanthrin B, cruciferane, and rice metabolites.

引用

页码：5962 / 5965

页数：4

共 38 条

[1] Albericio F., 2013, ADV ORG SYNTH, V4, P3
[2] Stereoselective anhydride openings
Atodiresei, Luliana
Schiffers, Ingo
Bolm, Carsten
[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5683 - 5712
[3] A Dual Arylboronic Acid-Aminothiourea Catalytic System for the Asymmetric Intramlecular Hetero-Michael Reaction of α,β-Unsaturated Carboxylic Acids
Azuma, Takumi
Murata, Akihiro
Kobayashi, Yusuke
Inokuma, Tsubasa
Takemoto, Yoshiji
[J]. ORGANIC LETTERS, 2014, 16 (16) : 4256 - 4259
[4] Organocatalytic Enantioselective Decarboxylative Aldol Reaction of Malonic Acid Half Thioesters with Aldehydes
Bae, Han Yong
Sim, Jae Hun
Lee, Ji-Woong
List, Benjamin
Song, Choong Eui
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (46) : 12143 - 12147
[5] Isolation and Cytotoxicity Evaluation of the Chemical Constituents from Cephalantheropsis gracilis
Chang, Chi-Fen
Hsu, Yu-Lin
Lee, Chao-Ying
Wu, Chia-Hua
Wu, Yang-Chang
Chuang, Ta-Hsien
[J]. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2015, 16 (02) : 3980 - 3989
[6] Alkaloids from the Root of Isatis indigotica
Chen, Minghua
Gan, Lishe
Lin, Sheng
Wang, Xiaoliang
Li, Li
Li, Yuhuan
Zhu, Chenggen
Wang, Yanan
Jiang, Bingya
Jiang, Jiandong
Yang, Yongchun
Shi, Jiangong
[J]. JOURNAL OF NATURAL PRODUCTS, 2012, 75 (06): : 1167 - 1176
[7] Asymmetric alcoholysis of cyclic anhydrides
Chen, YG
McDaid, P
Deng, L
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2965 - 2983
[8] Update 1 of: C2-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis
Desimoni, Giovanni
Faita, Giuseppe
Jorgensen, Karl Anker
[J]. CHEMICAL REVIEWS, 2011, 111 : PR284 - PR437
[9] Recent advances in enantioselective organocatalyzed anhydride desymmetrization and its application to the synthesis of valuable enantiopure compounds
Diaz de Villegas, Maria D.
Galvez, Jose A.
Etayo, Pablo
Badorrey, Ramon
Lopez-Ram-de-Viu, Pilar
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (11) : 5564 - 5587
[10] Stereoelectronic effects dictate mechanistic dichotomy between Cu(II)-catalyzed and enzyme-catalyzed reactions of malonic acid half thioesters
Fortner, Kevin C.
Shair, Matthew D.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) : 1032 - 1033

← 1 2 3 4 →