Catalytic asymmetric addition reactions leading to carbon-carbon bond formation: Phenyl and alkenyl transfer to aldehydes and alkynylation of α-imino esters

2006 ◽  
Vol 78 (2) ◽  
pp. 267-274 ◽  
Author(s):  
Jian-Xin Ji ◽  
Jing Wu ◽  
Lijin Xu ◽  
Chiu-Wing Yip ◽  
Kim Hung Lam ◽  
...  
Keyword(s):  
Bond Formation ◽  
Optically Active ◽  
Amino Acid Derivatives ◽  
Addition Reactions ◽  
Terminal Alkynes ◽  
Reaction Conditions ◽  
Carbon Carbon Bond ◽  
Catalytic Asymmetric ◽  
High Yields ◽  
Imino Esters

Optically active tertiary aminonaphthol ligands were obtained by a new, convenient procedure and were found to catalyze the enantioselective alkenyl and phenyl transfer to aldehydes in high yields and excellent enantiomeric excesses (ee's). The catalytic asymmetric introduction of alkynyl functionality to α-amino acid derivatives was realized by the direct addition of terminal alkynes to α-imino ester in the presence of chiral copper(I) complex under mild reaction conditions.

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

Nucleophilic addition at u 3 -alkyne clusters leading to carbon-carbon bond formation

1982 ◽  
Vol 308 (1501) ◽  
pp. 59-66 ◽  
Keyword(s):  
Bond Formation ◽  
Organic Ligand ◽  
Major Product ◽  
Unsaturated Hydrocarbon ◽  
Terminal Alkynes ◽  
Hydrogen Atoms ◽  
Metal Atoms ◽  
Carbon Carbon Bond ◽  
Anionic Species ◽  
A Minor

Reactions of nucleophiles with triosmium carbonyl clusters, especially those containing unsaturated hydrocarbon ligands, are discussed. Attack may be at CO, the metal atoms, at carbon of the organic ligand, or, where there are acidic metal-bound hydrogen atoms, deprotonation to give anionic clusters may occur. New results on the reactions of LiBHEt3 with p3-alkyne clusters of type Os3(CO)10 (RC2R') are considered in the light of the range of possible sites of attack. Protonation of anionic species that are formed gives hydrogenation products with or without the loss of CO. Os3H2(CO)9(RC2R') is usually a minor product, while C-C coupling leads to Os3H(CO)9(CRCR'COH) (in general the major product) and to Os3H(CO)9- (CRCR'CH). With terminal alkynes RC2H H-atom transfer accompanies C-C coupling to give Os3H(CO)9(RC—C =C H 2) in substantial amounts. The initial site of hydride attack (CO, alkyne or metal) is considered in the context of low-temperature 1H n.m.r. results.

scholarly journals Catalytic asymmetric carbon–carbon bond formation using alkenes as alkylmetal equivalents

2012 ◽  
Vol 4 (8) ◽  
pp. 649-654 ◽  
Author(s):  
Rebecca M. Maksymowicz ◽  
Philippe M. C. Roth ◽  
Stephen P. Fletcher
Keyword(s):  
Bond Formation ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Catalytic Asymmetric ◽  
Asymmetric Carbon

Catalytic Asymmetric Mono-Fluorination of α-Keto Esters: Synthesis of Optically Active β-Fluoro-α-Hydroxy and β-Fluoro-α-Amino Acid Derivatives

2012 ◽  
Vol 124 (19) ◽  
pp. 4659-4663 ◽  
Author(s):  
Shoko Suzuki ◽  
Yuki Kitamura ◽  
Sylvain Lectard ◽  
Yoshitaka Hamashima ◽  
Mikiko Sodeoka
Keyword(s):  
Amino Acid ◽  
Optically Active ◽  
Amino Acid Derivatives ◽  
Keto Esters ◽  
Catalytic Asymmetric

Chiral Catalysts Utilized in the Nucleophilic Addition of Dialkyl-zinc Reagents to Carbonyl Compounds

2020 ◽  
Vol 17 (8) ◽  
pp. 571-585
Author(s):  
Adnan Cetin
Keyword(s):  
Carbonyl Compounds ◽  
Nucleophilic Addition ◽  
Bond Formation ◽  
Research Topic ◽  
Chiral Ligands ◽  
Addition Reactions ◽  
Chiral Catalyst ◽  
Carbon Carbon Bond ◽  
Drug Synthesis ◽  
Active Research

The aim of this review is an overview of diverse dialkyl zinc pro-chiral aldehydes addition reactions. One way of conducting asymmetric reactions is through the use of chiral catalyst. Therefore, new chiral ligands have attracted considerable attention in organic chemistry. Carbon-carbon bond formation reactions are an active research topic. The addition of dialkyl zinc to pro-chiral aldehydes is one of these popular reactions. Also, the chiral amino alcohols are important substrates for drug synthesis. These chiral ligands can be prepared by a simple synthetic way from easily accessible starting materials. This article reviews current catalyst reactions with the addition of dialkyl zinc to carbonyl compounds.

ChemInform Abstract: Catalytic Asymmetric Monofluorination of α-Keto Esters: Synthesis of Optically Active β-Fluoro-α-hydroxy and β-Fluoro-α-amino Acid Derivatives.

ChemInform ◽  
2012 ◽  
Vol 43 (38) ◽  
pp. no-no
Author(s):  
Shoko Suzuki ◽  
Yuki Kitamura ◽  
Sylvain Lectard ◽  
Yoshitaka Hamashima ◽  
Mikiko Sodeoka
Keyword(s):  
Amino Acid ◽  
Optically Active ◽  
Amino Acid Derivatives ◽  
Keto Esters ◽  
Catalytic Asymmetric
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