L-Proline and HPESW Reaction: A Brief Fifty-Year Journey through Asymmetric Synthesis

被引：0

作者：

da Silva Lessa, Renato Correa ^{[1
]}

机构：

[1] Univ Fed Fluminense, Inst Quim, Dept Quim Organ, Outeiro Sao Joao Batista, BR-24020141 Niteroi, RJ, Brazil

来源：

REVISTA VIRTUAL DE QUIMICA | 2021年 / 13卷 / 02期

关键词：

Catalysis; green chemistry; Hajos-Parrish-Eder-Sauer-Wiechert; MEDICINAL CHEMISTRY; AMINO-ACID; ORGANOCATALYST; AMPLIFICATION; MECHANISM; CATALYSIS; STEROIDS; CASCADE;

D O I：

10.21577/1984-6835.20210009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

L-proline's potential as an asymmetric catalyst in the HPESW reaction started a rush for its mechanistical behavior comprehension. Over thirty years, many proposals were done based on theoretical chemical concepts. Only with the advances on computational chemistry and better reaction conditions, L-proline's mechanism in HPESW reaction could be finally uncovered. The mechanistical comprehension of its role in the HPESW reaction lead to changes in organic chemistry that impact fifty years after its discovery. Based on this context, this brief review will make an approach of L-proline trajectory, from the HPESW reaction perspective, over fifth years.

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页码：568 / 580

页数：13

相关论文

共 45 条

[1] IS THE MECHANISM OF THE PROLINE-CATALYZED ENANTIOSELECTIVE ALDOL REACTION RELATED TO BIOCHEMICAL PROCESSES [J].

AGAMI, C ;

PUCHOT, C ;

SEVESTRE, H .

TETRAHEDRON LETTERS, 1986, 27 (13) :1501-1504

[2] EXTENSION OF THE PROLINE-CATALYZED ASYMMETRIC ANNELATION TO DIKETONES - A NEW CASE OF KINETIC RESOLUTION [J].

AGAMI, C ;

LEVISALLES, J ;

SEVESTRE, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (07) :418-420

[3]

Armstrong A., 2016, MECHANISTIC UNDERSTA, pch6

[4] The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12911-12912

[5] Catalyst Repurposing Sequential Catalysis by Harnessing Regenerated Prolinamide Organocatalysts as Transfer Hydrogenation Ligands [J].

Bourgeois, Frederic ;

Medlock, Jonathan A. ;

Bonrath, Werner ;

Sparr, Christof .

ORGANIC LETTERS, 2020, 22 (01) :110-115

[6] Amplification of enantiomeric concentrations under credible prebiotic conditions [J].

Breslow, Ronald ;

Levine, Mindy S. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (35) :12979-12980

[7] Catalysis of the Hajos-Parrish-Eder-Sauer-Wiechert reaction by cis- and trans-4,5-methanoprolines:: Sensitivity of proline catalysis to pyrrolidine ring conformation [J].

Cheong, PHY ;

Houk, KN ;

Warrier, JS ;

Hanessian, S .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1111-1115

[8] Catalyst- and Base-Free Asymmetric Synthesis of Functionalized Prolines via One-Pot Cascade Reactions [J].

Cho, Hyunkyung ;

Kim, Jinju ;

Hyun Kim, Jae ;

Song, Yeonghun ;

Kim, Sanghee .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) :2941-2946

[9] Theoretical studies of stereoselectivities of intramolecular aldol cyclizations catalyzed by amino acids [J].

Clemente, FR ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11294-11302

[10] Computational evidence for the enamine mechanism of intramolecular Aldol reactions catalyzed by proline [J].

Clemente, FR ;

Houk, KN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (43) :5766-5768

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