The first organocatalytic asymmetric synthesis of 3-substituted isoindolinones

被引：43

作者：

More, Vijaykumar ^{[1
]}

Rohlmann, Renate ^{[2
]}

Mancheno, Olga Garcia ^{[2
]}

Petronzi, Carmen ^{[1
]}

Palombi, Laura ^{[1
]}

De Rosa, Antonio ^{[1
]}

Di Mola, Antonia ^{[3
]}

Massa, Antonio ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim & Biol, I-84084 Fisciano, SA, Italy

[2] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

[3] Univ Salerno, Dipartimento Sci Farmaceut, I-84084 Fisciano, SA, Italy

来源：

RSC ADVANCES | 2012年 / 2卷 / 09期

关键词：

DYNAMIC COMBINATORIAL RESOLUTION; ALDOL ADDITION; ENANTIOSELECTIVE SYNTHESIS; DERIVATIVES; MAPPICINE; ALDEHYDES; EFFICIENT; KETONES; ACCESS; AGENTS;

D O I：

10.1039/c2ra20231j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we describe the first asymmetric organocatalytic synthesis of 3-substituted isoindolinones in a convenient aldol-cyclization-rearrangement tandem reaction of malonates with 2-cyanobenzaldehyde. Bifunctional thiourea-cinchona catalysts proved to be particularly effective, giving the title compounds in high yields and moderate to good enantiomeric excesses. Moreover an efficient process of reverse crystallization led to a further enrichment up to >99% ee.

引用

页码：3592 / 3595

页数：4

共 50 条

[1] Asymmetric synthesis of 3-substituted isoindolinones: Application to the total synthesis of (+)-lennoxamine
Comins, DL
Schilling, S
Zhang, YC
ORGANIC LETTERS, 2005, 7 (01) : 95 - 98
[2] Facile synthesis of 3-substituted isoindolinones
Al-Jaroudi, Zainab
Mohapatra, Prabhu P.
Jha, Amitabh
TETRAHEDRON LETTERS, 2016, 57 (07) : 772 - 777
[3] Asymmetric Synthesis of 3-Substituted Isoindolinones by Direct Alkylation of Chiral N-tert-Butylsulfinyl-isoindolinones
Yin, Qiang
Li, Zhilong
He, Jiaxin
Lai, Yang
Zhang, Qianli
Sun, Haiying
JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (09): : 3501 - 3506
[4] Organocatalytic Asymmetric Transformations of 3-Substituted 3-Hydroxyisoindolinones
Glavac, Danijel
Gredicak, Matija
SYNLETT, 2017, 28 (08) : 889 - 897
[5] Chiral bifunctional organocatalysts for enantioselective synthesis of 3-substituted isoindolinones
Hu, Xiao-Mu
Zhang, Rui
Dong, Hai
Jia, Yan-Yan
Bao, Guo-Qiang
Wang, Ping-An
RSC ADVANCES, 2023, 13 (35) : 24460 - 24465
[6] Asymmetric synthesis of 3-substituted γ- and δ-sultams
Enders, D
Moll, A
Bats, JW
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (05) : 1271 - 1284
[7] Rh(I)-Catalyzed Asymmetric Synthesis of 3-Substituted Isoindolinones through CO Gas-Free Aminocarbonylation
Fujioka, Masahiko
Morimoto, Tsumoru
Tsumagari, Takayuki
Tanimoto, Hiroki
Nishiyama, Yasuhiro
Kakiuchi, Kiyomi
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (06): : 2911 - 2923
[8] Organocatalytic asymmetric hydroxymethylation of isoindolinones with paraformaldehyde
Francesco Scorzelli
Antonia Di Mola
Rosanna Filosa
Antonio Massa
Monatshefte für Chemie - Chemical Monthly, 2018, 149 : 723 - 727
[9] Organocatalytic asymmetric hydroxymethylation of isoindolinones with paraformaldehyde
Scorzelli, Francesco
Di Mola, Antonia
Filosa, Rosanna
Massa, Antonio
MONATSHEFTE FUR CHEMIE, 2018, 149 (04): : 723 - 727
[10] Organocatalytic asymmetric 5-hydroxypyrrolidine synthesis:: a highly enantioselective route to 3-substituted proline derivatives
Rios, Ramon
Ibrahem, Ismail
Vesely, Jan
Sunden, Henrik
Cordova, Armando
TETRAHEDRON LETTERS, 2007, 48 (49) : 8695 - 8699

← 1 2 3 4 5 →