scholarly journals Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines

2012 ◽  
Vol 8 ◽  
pp. 1668-1694 ◽  
Author(s):  
Chittaranjan Bhanja ◽  
Satyaban Jena ◽  
Sabita Nayak ◽  
Seetaram Mohapatra
Keyword(s):  
Enantioselective Synthesis ◽  
Synthetic Methods ◽  
Addition Reactions ◽  
Chiral Molecules ◽  
Cyclization Reactions ◽  
Central Importance ◽  
One Pot ◽  
Chiral Amine ◽  
Synthetic Compounds ◽  
Bioactive Natural Products

Enantioselective organocatalysis has become a field of central importance within asymmetric chemical synthesis and appears to be efficient approach toward the construction of complex chiral molecules from simple achiral materials in one-pot transformations under mild conditions with high stereocontrol. This review addresses the most significant synthetic methods reported on chiral-amine-catalyzed tandem Michael conjugate addition of heteroatom-centered nucleophiles to α,β-unsaturated compounds followed by cyclization reactions for the enantioselective construction of functionalized chiral chromenes, thiochromenes and 1,2-dihydroquinolines in optically enriched forms found in a myriad of bioactive natural products and synthetic compounds.

Metal-, and Organocatalyst-Free One-Pot Assembly of Chiral Aza-Tricyclic Molecules: Creating Six Contiguous Stereocenters from 2-D-Structures and an Amino Acid

2020 ◽  
Author(s):  
Dung Do
Keyword(s):  
Amino Acid ◽  
Chemical Space ◽  
Structural Diversity ◽  
Therapeutic Agents ◽  
Chiral Molecules ◽  
One Pot ◽  
Complex Molecules ◽  
Chiral Catalyst ◽  
Chiral Complex ◽  
Free Process

<p>Chiral molecules with their defined 3-D structures are of paramount importance for the study of chemical biology and drug discovery. Having rich structural diversity and unique stereoisomerism, chiral molecules offer a large chemical space that can be explored for the design of new therapeutic agents.<sup>1</sup> Practically, chiral architectures are usually prepared from organometallic and organocatalytic processes where a transition metal or an organocatalyst is tailor-made for desired reactions. As a result, developing a method that enables rapid assembly of chiral complex molecules under metal- and organocatalyst-free condition represents a daunting challenge. Here we developed a straightforward route to create a chiral 3-D structure from 2-D structures and an amino acid without any chiral catalyst. The center of this research is the design of a <a>special chiral spiroimidazolidinone cyclohexadienone intermediate</a>, a merger of a chiral reactive substrate with multiple nucleophillic/electrophillic sites and a transient organocatalyst. <a>This unique substrate-catalyst (“subcatalyst”) dual role of the intermediate enhances </a><a>the coordinational proximity of the chiral substrate and catalyst</a> in the key Aza-Michael/Michael cascade resulting in a substantial steric discrimination and an excellent overall diastereoselectivity. Whereas the “subcatalyst” (hidden catalyst) is not present in the reaction’s initial components, which renders a chiral catalyst-free process, it is strategically produced to promote sequential self-catalyzed reactions. The success of this methodology will pave the way for many efficient preparations of chiral complex molecules and aid for the quest to create next generation of therapeutic agents.</p>

Short syntheses of 1-substituted dibenzothiophene derivatives

2021 ◽  
Vol 19 (9) ◽  
pp. 2000-2007
Author(s):  
Erin N. Welsh ◽  
Katherine N. Robertson ◽  
Alexander W. H. Speed
Keyword(s):  
Cross Coupling ◽  
One Pot ◽  
Chiral Amine ◽  
Rapid Access

A one-pot double benzyne cascade allows rapid access to 1-substituted dibenzothiophene derivatives, including cross-coupling partners and a chiral amine.

The first peripherally masked thiol dendrimers: a facile and highly efficient functionalization strategy of polyester dendrimers via one-pot xanthate deprotection/thiol–acrylate Michael addition reactions

2014 ◽  
Vol 50 (50) ◽  
pp. 6574-6577 ◽  
Author(s):  
Sam E. R. Auty ◽  
Oliver Andrén ◽  
Michael Malkoch ◽  
Steven P. Rannard
Keyword(s):  
Michael Addition ◽  
Addition Reactions ◽  
One Pot ◽  
Highly Efficient

We present the first xanthate surface functional dendrimers which undergo rapid one-pot deprotection to thiols and subsequent acrylate Michael addition .

Divergent synthesis of chiral heterocycles via sequencing of enantioselective three-component reactions and one-pot subsequent cyclization reactions

2015 ◽  
Vol 51 (53) ◽  
pp. 10612-10615 ◽  
Author(s):  
Min Tang ◽  
Dong Xing ◽  
Haoxi Huang ◽  
Wenhao Hu
Keyword(s):  
Cyclization Reactions ◽  
One Pot ◽  
Highly Efficient ◽  
Subsequent Cyclization

A highly efficient sequencing of enantioselective three-component reactions with a variety of one-pot subsequent cyclization reactions was developed.

An Efficient Organocatalysis: A One-Pot Highly Enantioselective Synthesis of α-Aminophosphonates

2013 ◽  
Vol 2013 (24) ◽  
pp. 5509-5516 ◽  
Author(s):  
Prashant B. Thorat ◽  
Santosh V. Goswami ◽  
Rupali L. Magar ◽  
Bhagwan R. Patil ◽  
Sudhakar R. Bhusare
Keyword(s):  
Enantioselective Synthesis ◽  
One Pot

Recent advance in ester synthesis by Multi Component Reactions (MCRs): A Review

2021 ◽  
Vol 25 ◽  
Author(s):  
Dhaval B. Patel ◽  
Jagruti A. Parmar ◽  
Siddharth S. Patel ◽  
Unnati J. Naik ◽  
Hitesh D. Patel
Keyword(s):  
Multicomponent Reactions ◽  
Medicinal Chemistry ◽  
Reaction Times ◽  
Synthetic Methods ◽  
Ester Synthesis ◽  
One Pot ◽  
Wide Range ◽  
Recent Developments ◽  
Ester Linkage ◽  
The One

: The synthesis of ester containing heterocyclic compounds via multicomponent reaction is one of the most preferable process in the synthetic organic chemistry and medicinal chemistry. Compounds containing ester linkage have a wide range of biological application in the pharmaceutical field. Therefore, many method have been developed for the synthesis of these type of derivatives. However, some of them are carried out in the presence of toxic solvents and catalysts, with lower yields, longer reaction times, low selectivities and by-products. Thus, the development of new synthetic methods for the ester synthesis is required in the medicinal chemistry. As we know, multicomponent reactions (MCRs) are a powerful tool towards the one-pot ester synthesis, so in this article we have reviewed the recent developments in ester synthesis. This work covers selected explanation of methods via multicomponent reactions to explore the methodological development in ester synthesis.

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