Recent advances in the application of the Oppolzer camphorsultam as a chiral auxiliary

Heravi, Majid Μ.; Zadsirjan, Vahideh

doi:10.1016/j.tetasy.2014.07.001

Cited by 56 publications

(37 citation statements)

References 153 publications

(116 reference statements)

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“…[29] Furthermore, synthetic AAs are widely applied in the field of asymmetric catalysis where they are used as starting materials for the synthesis of chiral organocatalysts, as chiral ligands or starting materials for chiral ligands in metal complex based catalysis, [30][31][32][33][34] and in the design of novel artificial metalloenzymes. [35][36][37][38][39][40][41] Today, the standard methods for the asymmetric synthesis of non-proteinogenic AAs are the Strecker reaction, [42][43][44] the derivatization of glycine derivatives employing chiral auxiliaries [3,[5][6][7][45][46][47] and chiral catalysts, [48][49][50][51][52][53][54][55] and the hydrogenation of dehydroamino acid derivatives. [56][57][58] However, the reported methods have inherent limitations.…”

Section: Introductionmentioning

confidence: 99%

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Advances in Asymmetric Amino Acid Synthesis Enabled by Radical Chemistry

2020

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Chiral amino acids (AAs), being the main "building" blocks of the living organisms, are also an important class of organic compounds which broadly applied in synthetic chemistry, biochemistry, catalysis and the designing of new drugs. According to the industrial-commodity market, chiral non-proteinogenic AAs containing various functional groups come to the fore. To date, radical cross-coupling reactions are becoming an option as an attractive powerful tool for AA syntheses. Owing to mild reaction conditions and high functional-group tolerance, radical chemistry represents an ideal strategy for the synthesis of challenging complex non-proteinogenic AAs. Moreover, the radical cross-coupling allows introducing AA residue into drug scaffolds and natural compounds. In the present review, we wish to summarize and discuss all the reported to date methods of the asymmetric synthesis of AAs using radical chemistry by presenting a comprehensive account of the literature in this field going back to 1990. We especially emphasize on a radical chemistry approach and, exclusively, on stereoselective synthesis of various α-, β-, γ-AAs and derivatives employing a different type of radical initiators starting from AIBN and organostannes and ending with powerful photoredox catalysis. Furthermore, the mechanism of the reported reactions will be discussed. Radicals Generated from AA Derivatives in Conjugate Additions 6.1. Radicals Generated from α-Substituted Glycine Derivatives in AA Synthesis 6.2. Modification of Chiral AA Side Chain by Radical Chemistry 7.

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Section: Introductionmentioning

confidence: 99%

“…Today, the standard methods for the asymmetric synthesis of non‐proteinogenic AAs are the Strecker reaction, the derivatization of glycine derivatives employing chiral auxiliaries and chiral catalysts, and the hydrogenation of dehydroamino acid derivatives . However, the reported methods have inherent limitations.…”

Section: Introductionmentioning

confidence: 99%

Advances in Asymmetric Amino Acid Synthesis Enabled by Radical Chemistry

2020

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“…Compared to the classical methods for oxidation and reduction of organic compounds, organic electrosynthesis is generally considered as a green chemistry due to the use of electric current instead of redox reagents to provide the opportunity for reducing the overall cast, waste generation and energy consumption of a process. We are interested in applications of electrochemical synthesis and name reaction, in organic chemistry. In this review, we focused on the electrosynthesis as green strategy in MAR as a basic and very important and versatile classic organic reaction.…”

Section: Introductionmentioning

confidence: 99%

Electrochemically Induced Michael Addition Reaction: An Overview

Fotouhi

Heravi

Zadsirjan

et al. 2018

The Chemical Record

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Due to its high potential for the formation of carbon‐carbon bonds, Michael addition reaction is one of the closest reactions to the heart of synthetic organic chemists. Electrochemistry presents a very stimulating and divergent resource for selective oxidation and reduction in organic chemistry, generating activated species, for example radical anions or radical cations. In this review, we try to underscore usefulness of electrogenerated Michael addition reaction with the hope of encouraging synthetic organic chemists to contemplate it, as an efficient and green strategy when it is required in their designed multi‐step reaction pathways.

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“…In 2003, a comprehensive and invaluable review entitled 'Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions' by Hayashi et al appeared. 32 We are interested in the asymmetric synthesis, [35][36][37][38][39][40][41][42][43] and applications of named reactions in the total synthesis of natural products which usually use asymmetric synthesis in one or more steps in their multi-step synthesis. [44][45][46][47][48] Due to the increasing number of articles published concerning asymmetric 1,4-addition reactions, catalyzed by Rh-complexes, we were prompted to update the invaluable review by Hayashi et al in 2003.…”

Section: Introductionmentioning

confidence: 99%

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

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Rh-catalyzed asymmetric 1,4-addition reactions to a,b-unsaturated carbonyl and related compounds: an update Available online xxxx Dedicated to my son, OMID on the occasion of his 35th birthday. a b s t r a c tThe Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to an appropriate receptor has been a growing area of research over the last decade. The receptors for such a 1,4-addition reaction are chiefly a,b-unsaturated ketones, esters, amides, enones, nitroalkenes, and occasionally phosphonates etc. This reaction in the presence of chiral rhodium complexes introduce the aryl and alkenyl groups at the b-position of the above electron poor olefins, enantioselectively. Chiral Rh complexes similar to other transition metals can be added to some electron poor olefins, in turn making them viable to attack by various organometallic reagents for highly enantioselective C-C bond formation. The Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to electron poor olefins has been reviewed in 2003. Due to the importance of the asymmetric C-C bond formation via 1,4-conjugate addition reactions and the number of such reactions catalyzed by Rh-complexes, in this review we highlight the recent advances in Rh-complex asymmetric catalyzed 1,4-addition reactions since 2003.

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Recent advances in the application of the Oppolzer camphorsultam as a chiral auxiliary

Cited by 56 publications

References 153 publications

Advances in Asymmetric Amino Acid Synthesis Enabled by Radical Chemistry

Advances in Asymmetric Amino Acid Synthesis Enabled by Radical Chemistry

Electrochemically Induced Michael Addition Reaction: An Overview

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

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