Nickel-Catalyzed Asymmetric Cross-Electrophile Coupling Reactions

Synlett ◽  
2020 ◽  
Vol 31 (19) ◽  
pp. 1843-1850 ◽  
Author(s):  
Chuan Wang ◽  
Youxiang Jin
Keyword(s):  
Asymmetric Catalysis ◽  
Carbonyl Compounds ◽  
Ring Opening ◽  
Research Field ◽  
Optically Active ◽  
Coupling Reactions ◽  
Mild Conditions ◽  
Novel Approach ◽  
Ring Opening Reactions ◽  
Two Component

The merger of cross-electrophile coupling and asymmetric catalysis provides a novel approach to the preparation of optically active compounds. This method is often endowed with high step economy, mild conditions, and excellent tolerance of functional groups. Recent advances in the research field of nickel-catalyzed asymmetric cross-electrophile coupling reactions are highlighted in this concise Synpacts article.1 Introduction2 Asymmetric Cross-Electrophile Coupling Reactions between Organohalides3 Asymmetric Electrophilic Ring-Opening Reactions4 Asymmetric Electrophilic Difunctionalization of Alkenes4.1 Two-Component Electrophilic Difunctionalization of Alkenes Involving Arylnickelation as an Enantiodetermining Step4.2 Two-Component Electrophilic Difunctionalization of Alkenes Involving Carbamoylnickelation as an Enantiodetermining Step4.3 Three-Component Electrophilic Difunctionalization of Alkenes5 Asymmetric Electrophilic Functionalization of Carbonyl Compounds6 Summary

Asymmetric catalysis in aqueous media

2007 ◽  
Vol 79 (2) ◽  
pp. 235-245 ◽  
Author(s):  
Shū Kobayashi
Keyword(s):  
Asymmetric Catalysis ◽  
Lewis Acids ◽  
Ring Opening ◽  
Acid Catalysis ◽  
Aqueous Media ◽  
Asymmetric Reactions ◽  
Epoxide Ring ◽  
Mild Conditions ◽  
Ring Opening Reactions ◽  
Bipyridine Ligand

Lewis acid catalysis has attracted much attention in organic synthesis because of unique reactivity and selectivity attained under mild conditions. Although various kinds of Lewis acids have been developed and applied in industry, these Lewis acids must be generally used under strictly anhydrous conditions. The presence of even a small amount of water handles the reactions owing to preferential reactions of the Lewis acids with water rather than the substrates. In contrast, rare earth and other metal complexes have been found to be water-compatible. Several catalytic asymmetric reactions in aqueous media, including hydroxymethylation of silicon enolates with an aqueous solution of formaldehyde in the presence of Sc(OTf)3-chiral bipyridine ligand or Bi(OTf)3-chiral bipyridine ligand, Sc- or Bi-catalyzed asymmetric meso-epoxide ring-opening reactions with amines, and asymmetric Mannich-type reactions of silicon enolates with N-acylhydrazones in the presence of a chiral Zn catalyst have been developed. Water plays key roles in these asymmetric reactions.

Lead(IV) acetate oxidative ring-opening of 2,3-epoxy primary alcohols: a new entry to optically active α-hydroxy carbonyl compounds

2011 ◽  
Vol 52 (31) ◽  
pp. 4017-4020 ◽  
Author(s):  
Enrique Alvarez-Manzaneda ◽  
Rachid Chahboun ◽  
Esteban Alvarez ◽  
Ramón Alvarez-Manzaneda ◽  
Pedro E. Muñoz ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Ring Opening ◽  
Optically Active ◽  
Primary Alcohols ◽  
New Entry

Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles

2015 ◽  
Vol 13 (17) ◽  
pp. 4855-4858 ◽  
Author(s):  
Ren-Rong Liu ◽  
Shi-Chun Ye ◽  
Chuan-Jun Lu ◽  
Bin Xiang ◽  
Jianrong Gao ◽  
...  
Keyword(s):  
Ring Opening ◽  
Bond Cleavage ◽  
Mild Conditions ◽  
Efficient Access ◽  
Ring Opening Reactions ◽  
Novel Method

A novel method for the C–C bond cleavage of cyclopropanes was developed by gold-catalyzed cycloisomerization of 2-(1-alkynyl-cyclopropyl)pyridine with nucleophiles, which provides efficient access to structurally diverse indolizines under mild conditions.

DABCO as a Base and an Organocatalyst in Organic Synthesis: A Review

2020 ◽  
Vol 7 (2) ◽  
pp. 146-162
Author(s):  
Dinesh K. Jangid
Keyword(s):  
Organic Synthesis ◽  
Ring Opening ◽  
High Selectivity ◽  
Solid Catalyst ◽  
Cycloaddition Reactions ◽  
Coupling Reactions ◽  
Henry Reaction ◽  
Environmental Friendly ◽  
Ring Opening Reactions ◽  
Catalytic Applications

One of the organocatalysts 1,4-diazabicyclo[2.2.2]octane (DABCO) is an excellent solid catalyst in a number of reactions. It is also a good nucleophile and a base in numerous reactions for the synthesis of heterocycles. DABCO catalyzes many reactions like cycloaddition reactions, coupling reactions, Baylis-Hillman reaction, Henry reaction, ring opening reactions, etc. One more advanced feature of these reactions is that they proceed through environmental friendly pathway. DABCO has more advantages than other organic catalysts because it is an inexpensive, non.toxic base, an ecofriendly and a highly reactive catalyst for building of organic frameworks, which produce the desired products in excellent yields with high selectivity. Many catalytic applications of DABCO have been reported for the synthesis of an organic framework which has been discussed in this review.

Thiophene ring-opening reactions IV. Facile generation of novel ethyl 4-hydroxy-6-thioxonicotinate─1,3,4- thiadiazoline hybrids

2021 ◽  
Vol 18 ◽  
Author(s):  
Mohammed M. Abadleh ◽  
Ahmad H. Abdullah ◽  
Jalal A. Zahra ◽  
Salim S. Sabri ◽  
Firas F. Awwadi ◽  
...  
Keyword(s):  
Single Crystal ◽  
Spectral Data ◽  
1H Nmr ◽  
13C Nmr ◽  
Ring Opening ◽  
Thiophene Ring ◽  
X Ray Diffraction ◽  
X Ray ◽  
Mild Conditions ◽  
Ring Opening Reactions

: A set of triethylammonium 4-oxo-6-pyridinethiolate–1,3,4-thiadiazoline hybrids (3a-e) were prepared via the reaction of ethyl 2-chloro-6-cyclopropyl-3- nitro-4-oxothieno[2,3-b]pyridine- 5-carboxylate (2) with the appropriate thiobenzoyl- hydrazide (1a-e) in acetonitrile and triethylamine. These hybrids were readily converted, under neutral mild conditions, into the corresponding 4-hydroxy-6-thioxopyridine –thiadiazoline hybrids (5a-e). The structures of the latter set are supported by HRMS, 1H NMR and 13C NMR spectral data and further confirmed by single-crystal X-ray diffraction studies. Alkylation of these hybrids in the presence of triethylamine occurred exclusively at the 6-thioxosulfur, yielding the respective 6-sulfanyl derivatives (6a-c).

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