scholarly journals Recent advances in organocatalytic asymmetric oxa-Michael addition triggered cascade reactions

2020 ◽  
Vol 7 (20) ◽  
pp. 3266-3283
Author(s):  
Yu Wang ◽  
Da-Ming Du
Keyword(s):  
Michael Addition ◽  
Cascade Reactions ◽  
Recent Advances

In this review, we summarized recent advances in organocatalytic asymmetric oxa-Michael addition triggered cascade reactions.

Efficient synthesis of chiral cyclic acetals by metal and Brønsted acid co-catalyzed enantioselective four-component cascade reactions

2014 ◽  
Vol 50 (17) ◽  
pp. 2196-2198 ◽  
Author(s):  
Lin Qiu ◽  
Xin Guo ◽  
Chaoqun Ma ◽  
Huang Qiu ◽  
Shunying Liu ◽  
...  
Keyword(s):  
Michael Addition ◽  
Cascade Reactions ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Efficient Synthesis ◽  
Mannich Reactions ◽  
Cyclic Acetals ◽  
Brönsted Acid

Four-component Mannich reactions subsequently followed by an intramolecular oxo-Michael addition were developed to efficiently produce chiral cyclic acetals with high diastereoselectivity and enantioselectivity.

Recent Advances in Cascade Reactions Initiated by Alcohol Oxidation

ChemCatChem ◽  
2016 ◽  
Vol 9 (2) ◽  
pp. 217-246 ◽  
Author(s):  
Ana Maria Faisca Phillips ◽  
Armando J. L. Pombeiro ◽  
Maximilian N. Kopylovich
Keyword(s):  
Alcohol Oxidation ◽  
Cascade Reactions ◽  
Recent Advances

scholarly journals Synthesis of indanes via carbene-catalyzed single-electron-transfer processes and cascade reactions

2017 ◽  
Vol 53 (87) ◽  
pp. 11952-11955 ◽  
Author(s):  
Yuhuang Wang ◽  
Xingxing Wu ◽  
Yonggui Robin Chi
Keyword(s):  
Electron Transfer ◽  
Michael Addition ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Transfer Processes ◽  
Electron Transfer Processes

An NHC-catalyzed cascade reaction involving an SET process and two sequential Michael addition steps for the synthesis of indanes is disclosed.

Recent advances of organocatalytic enantioselective Michael-addition to chalcone

2015 ◽  
Vol 42 (4) ◽  
pp. 2731-2747 ◽  
Author(s):  
Sabita Nayak ◽  
Subhendu Chakroborty ◽  
Sujitlal Bhakta ◽  
Pravati Panda ◽  
Seetaram Mohapatra
Keyword(s):  
Michael Addition ◽  
Recent Advances

Synthetic Approaches for Building Tricyclic Cage-like Motifs Found in Indoxamycins

2020 ◽  
Vol 24 ◽  
Author(s):  
Saqlain Haider ◽  
Ikhlas A. Khan ◽  
Hanfeng Ding ◽  
Amar G. Chittiboyina
Keyword(s):  
Natural Products ◽  
Michael Addition ◽  
Claisen Rearrangement ◽  
Biological Activities ◽  
Cascade Reactions ◽  
Biological Properties ◽  
Starting Material ◽  
Central Core ◽  
Chemical Transformations ◽  
One Pot

Abstract:: Indoxamycins A-F, a novel class of polyketides, were isolated from the saline culture of marine-derived actinomyces by Sato et al. in 2009. Intriguing stereochemical complexity involving tricyclic [5.5.6] cage-like structures with six consecutive chiral centers challenged many organic chemists. Chemical ingenuity, implementation of pioneered reactions along with fine chemical transformations allowed not only the rapid construction of the central core but also allowed minor structural revision and paved the information to delineate the absolute stereostructures of these complex polyketide marine natural products. To achieve the central core structure in indoxamycins A-F, reactions like the Ireland- Claisen rearrangement, an enantioselective 1,6-enyne reductive cyclization, and one-pot cascade reactions of 1,2- addition/oxa-Michael/methylenation were employed. Using the chiral pool approach, the readily available R-carvone was employed as a cost-effective starting material to achieve the concise total syntheses of (-)-indoxamycins A and B, in which Pauson-Khand, Cu-catalyzed Michael addition and tandem retro-oxa-Michael addition/1,2-addition/oxa-Michael addition reactions were employed. The antipodes, (+)-indoxamycins can be easily accessed by simply switching to S-carvone as the starting material. Synthetically prepared indoxamycins A-F are devoid of antiproliferative properties which disagrees with the work reported by Sato and co-workers for (-)-indoxamycins A and F. Nevertheless, ready access to such complex natural products allows probing the untapped potential biological activities of these polyketides including cytotoxicity. A concise overview of interesting, key chemical transformations including named reactions in establishing the architecture of indoxamycins was compiled to inspire organic chemists and help reinvigorate the development of novel strategies for the asymmetric synthesis as well as the development of novel derivatives of indoxamycins with unique physicochemical and biological properties.

Recent Advances in Synthesis of Benzazoles via Imines

2020 ◽  
Vol 24 (17) ◽  
pp. 1897-1942
Author(s):  
Ran An ◽  
Mengbi Guo ◽  
Yingbo Zang ◽  
Hang Xu ◽  
Zhuang Hou ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Recent Progress ◽  
Cascade Reactions ◽  
Biologically Active ◽  
Coupling Reactions ◽  
Condensation Reactions ◽  
Recent Advances

Imines, versatile intermediates for organic synthesis, can be exploited for the preparation of diverse classes of biologically active benzazoles. Because of the special characteristics of the C=N bond, imines can be simultaneously used in the synthesis of 1,3-benzazoles and 1,2-benzazoles. With the development of imine synthesis, a variety of novel cascade reactions for benzazole synthesis have been reported in the last decade. Therefore, there is a strong need to elucidate the recent progress in the formation of various classes of benzazoles, including benzimidazoles, benzoxazoles, benzothiazoles, indazoles, and benzisoxazoles, via imines obtained by condensation reactions or oxidative/ redox coupling reactions

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