Well‐Defined Chiral Copper NHC Complex in the Asymmetric Conjugated β‐Borylation and One‐Pot Metathesis‐Asymmetric β‐Borylation Reactions

Jana, Anupam; Trzybiński, Damian; Woźniak, Krzysztof; Grela, Karol

doi:10.1002/chem.201704335

Cited by 13 publications

(4 citation statements)

References 60 publications

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“…Since the isolation and full characterization of a free N-heterocyclic carbene (NHC), 56 catalysis mediated by NHC-based metal complexes has emerged as a powerful method for the construction of the carbon-carbon bond. [57][58][59][60][61][62][63][64] Nevertheless, Cu-NHC-catalyzed enantioselective reactions had been underdeveloped until Sawamura and coworkers reported 65 regio-and enantioselective allyl-allyl coupling between substituted allyllic boronates and phosphate (Scheme 17). Remarkably, the limitation of regioselectivity faced by Feringa and co-workers was solved when they reported copper-catalyzed enantioselective allyl-allyl crosscoupling between (Z)-allylic phosphates and allyl boronates using phenol/NHC chiral ligands.…”

Section: Copper-catalyzed Couplingmentioning

confidence: 99%

Recent development of allyl–allyl cross-coupling and its application in natural product synthesis

Ravichandiran

Jana

2023

Org. Chem. Front.

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Section: Copper-catalyzed Couplingmentioning

confidence: 99%

Recent development of allyl–allyl cross-coupling and its application in natural product synthesis

Ravichandiran

Jana

2023

Org. Chem. Front.

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“…Further, inspired by Lüning's work, [58] the Grela group designed a new type of macrocyclic NHC‐based copper catalyst ( Cat‐3 ), for the enantioselective β‐borylation of α,β‐unsaturated esters (Scheme 9d) [59] . The chiral environment created by the phenyl substituents in the backbone and the alkyl chain connecting the two aromatic wings of the NHC ligand resulted in high yield and enantioselectivity.…”

Section: Copper Catalyzed β‐Borylationmentioning

confidence: 99%

Development of Methods to the Synthesis of β‐Boryl Acyls, Imines and Nitriles

Das

Mahato

Hazra

et al. 2022

The Chemical Record

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Organoboron compounds are highly important and versatile synthetic intermediates for the preparation of a wide range of organic molecules. Organoboron compounds have drawn significant attention among organic chemists due to their Lewis acidic property, non-toxicity, and commercial availability. Over the last several decades, there has been a substantial development of new organoboron compounds, useful in organic synthesis. Among all other organoboron compounds, β-boryl carbonyl compounds are the important ones. The β-boryl compounds have appeared as promising intermediates for various synthetic transformations. The 1,4-conjugate addition of diboron reagents to carbon-carbon double bond in the presence of different transition-metal catalysts has been extensively reported by various research groups across the globe. This mini-review outlines the numerous racemic as well as asymmetric β-borylation methods developed to date.

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“…In 2018, a similar strategy was developed by Grela and co-workers (Scheme 12). 31 In this case, the key 18membered macrocycle 64 was formed by the ring-closing metathesis reaction of a diene 63 bearing the chiral NHC core.…”

Section: Condensation Reductionmentioning

confidence: 99%

Synthetic Approaches to Chiral Non-C 2-symmetric N-Heterocyclic Carbene Precursors

Czerwiński¹,

Michalak

2019

Synthesis

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N-Heterocyclic carbenes and their metal complexes have found applications in many organic transformations. Apart from the privileged C 2-symmetry present in modern enantioselective catalysis, ligands bearing C 1-symmetry have witnessed growing attention due to the better control of process stereoselectivity in many cases. The present review summarizes, for the first time, the seminal synthetic efforts for the preparation of N-heterocyclic carbene precursors exhibiting C 1-symmetry. The well-established methods will be discussed in the light of recent achievements, giving a direct opportunity for comparison of the existing methods, and simultaneously a chance to find the best synthetic pathway for the ideal chiral ligand.1 Introduction2 Five-Membered Rings2.1 Five-Membered Saturated (Imidazolinium) Ring2.1.1 Amino Alcohol Derivatives2.1.2 Amino Acid Derivatives2.1.3 Amine and Diamine Derivatives2.2 Five-Membered Unsaturated Ring2.2.1 Cyclization Strategy2.2.2 Functionalization of the Existing N-Imidazole Ring3 Triazolium Salts3.1 Substitution in Oxadiazolium Salts3.2 Lactam-Derived Triazolium NHC (The Leeper and Knight Methodology)3.3 Monoterpenoid-Derived NHC Triazolium Salts3.4 Modifications of the Existing Triazole Ring4 Thiazole-Derived Salts4.1 Cyclization of a Thiazolium Ring4.2 Modifications of the Existing Thiazole Ring5 Summary and Outlook

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Well‐Defined Chiral Copper NHC Complex in the Asymmetric Conjugated β‐Borylation and One‐Pot Metathesis‐Asymmetric β‐Borylation Reactions

Cited by 13 publications

References 60 publications

Recent development of allyl–allyl cross-coupling and its application in natural product synthesis

Recent development of allyl–allyl cross-coupling and its application in natural product synthesis

Development of Methods to the Synthesis of β‐Boryl Acyls, Imines and Nitriles

Synthetic Approaches to Chiral Non-C 2-symmetric N-Heterocyclic Carbene Precursors

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