A sustainable catalytic enantioselective synthesis of norstatine derivatives

2019 ◽  
Vol 17 (45) ◽  
pp. 9792-9798
Author(s):  
Taoda Shi ◽  
Changcheng Jing ◽  
Yu Qian ◽  
Xinfang Xu ◽  
Gopi Krishna Reddy Alavala ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Reusable Catalyst ◽  
Mechanistic Investigations ◽  
Synthetic Application

An unprecedented method with excellent ee, broad substrate scope, reliable scalability, improved safety, and reusable catalyst is described here along with its synthetic application and mechanistic investigations.

scholarly journals Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

2021 ◽  
Author(s):  
Zikun Wang ◽  
Zhansong Zhang ◽  
Wanjun Zhao ◽  
Paramasivam Sivaguru ◽  
Zanoni Giuseppe ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Functional Groups ◽  
Radical Addition ◽  
Single Step ◽  
Unsaturated Hydrocarbons ◽  
Radical Coupling ◽  
Extensive Range ◽  
Mechanistic Investigations ◽  
Sulfinyl Radical ◽  
Synthetic Application

Abstract Sulfinyl radicals – one of the fundamental classes of S-centered radicals – have eluded synthetic application in organic chemistry for over 60 years, despite their potential to assemble valuable sulfoxide compounds. Here we report the successful generation and use of sulfinyl radicals in a dual radical addition / radical coupling with unsaturated hydrocarbons, where readily-accessed sulfinyl sulfones serve as the sulfinyl radical precursor. The strategy provides an entry to a variety of previously inaccessible linear and cyclic disulfurized adducts in a single step, and demonstrates excellent tolerance to an extensive range of hydrocarbons and functional groups. Experimental and theoretical mechanistic investigations suggest that these reactions proceed through sequential sulfonyl and sulfinyl radical addition.

scholarly journals Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides

2017 ◽  
Vol 13 ◽  
pp. 1518-1523 ◽  
Author(s):  
Ryota Miyaji ◽  
Yuuki Wada ◽  
Akira Matsumoto ◽  
Keisuke Asano ◽  
Seijiro Matsubara
Keyword(s):  
Asymmetric Synthesis ◽  
Functional Groups ◽  
Enantioselective Synthesis ◽  
Chiral Compounds ◽  
Axially Chiral ◽  
Electrophilic Bromination ◽  
Mechanistic Investigations ◽  
Molecular Skeleton

Bifunctional organocatalysts bearing amino and urea functional groups in a chiral molecular skeleton were applied to the enantioselective synthesis of axially chiral benzamides via aromatic electrophilic bromination. The results demonstrate the versatility of bifunctional organocatalysts for the enantioselective construction of axially chiral compounds. Moderate to good enantioselectivities were afforded with a range of benzamide substrates. Mechanistic investigations were also carried out.

scholarly journals One-pot synthesis of (S)-2-(6-methoxynaphtalen-2-yl)propanoic acid, (S)-Naproxen using Preyssler and Keggin-type heteropolyacids as green and reusable catalysts

2009 ◽  
Vol 11 (3) ◽  
pp. 8-14 ◽  
Author(s):  
Ali Gharib ◽  
Mohsen Daneshtalab ◽  
J. Scheeren ◽  
Fatemeh Bamoharram ◽  
Mina Roshani ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Environmentally Benign ◽  
Propanoic Acid ◽  
Reusable Catalyst ◽  
One Pot ◽  
Keggin Type ◽  
One Pot Synthesis

One-pot synthesis of (S)-2-(6-methoxynaphtalen-2-yl)propanoic acid, (S)-Naproxen using Preyssler and Keggin-type heteropolyacids as green and reusable catalysts A simple, clean and environmentally benign route to the enantioselective synthesis of (S)-2-(6-methoxynaphtalen-2-yl)propanoic acid, (S)-Naproxen 3 is described by using Preyssler heteropolyacid, H14[NaP5W30O110], as a green and reusable catalyst in water and in the presence of 1-(6-methoxynaphthalen-2-yl)propan-1-one 1, D-mannitol 2. The products were obtained in very good yields.

scholarly journals Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Zikun Wang ◽  
Zhansong Zhang ◽  
Wanjun Zhao ◽  
Paramasivam Sivaguru ◽  
Giuseppe Zanoni ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Functional Groups ◽  
Radical Addition ◽  
Single Step ◽  
Unsaturated Hydrocarbons ◽  
Radical Coupling ◽  
Extensive Range ◽  
Mechanistic Investigations ◽  
Sulfinyl Radical ◽  
Synthetic Application

AbstractSulfinyl radicals – one of the fundamental classes of S-centered radicals – have eluded synthetic application in organic chemistry for over 60 years, despite their potential to assemble valuable sulfoxide compounds. Here we report the successful generation and use of sulfinyl radicals in a dual radical addition/radical coupling with unsaturated hydrocarbons, where readily-accessed sulfinyl sulfones serve as the sulfinyl radical precursor. The strategy provides an entry to a variety of previously inaccessible linear and cyclic disulfurized adducts in a single step, and demonstrates tolerance to an extensive range of hydrocarbons and functional groups. Experimental and theoretical mechanistic investigations suggest that these reactions proceed through sequential sulfonyl and sulfinyl radical addition.

Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

2021 ◽  
Author(s):  
Xin-Ming Xu ◽  
Ming Xie ◽  
Jiazhu Li ◽  
Mei-Xiang Wang
Keyword(s):  
Indole Alkaloid ◽  
Enantioselective Synthesis ◽  
High Yield ◽  
Tandem Reaction ◽  
Indole Derivatives

An exquisite Pybox/Cu(OTf)2-catalyzed asymmetric tandem reaction of tertiary enamides was developed, which enabled the expeditious synthesis of indolizino[8,7-b]indole derivatives in high yield, excellent enantioselectivity and diastereoselectivity.

Three-Component [1+1+1] Cyclopropanation with Ruthenium(II)

2018 ◽  
Author(s):  
Tanner C. Jankins ◽  
Robert R. Fayzullin ◽  
Eugene Khaskin
Keyword(s):  
Quaternary Carbon ◽  
Poor Control ◽  
One Step ◽  
Synthetic Routes ◽  
Mechanistic Investigations ◽  
Chiral Centers ◽  
Metal Catalyzed ◽  
The Right ◽  
Substituted Cyclopropanes

We report a one-step, Ru(II)-catalyzed cyclopropanation reaction that is conceptually different from the previously reported protocols that include Corey-Chaykovsky, Simmons-Smith, and metal catalyzed carbene attack on olefins. Under the current protocol, various alcohols are transformed into sulfone substituted cyclopropanes with excellent isolated yields and diastereoselectivities. This new reaction forms highly congested cyclopropane products with three new C–C bonds, three or two new chiral centers and one new quaternary carbon center. 22 examples of isolated substrates are given. Previously reported synthetic routes for similar substrates are all multi-step, linear routes that proceed with overall low yields and poor control of stereochemistry. Experimental mechanistic investigations suggest initial metal-catalyzed dehydrogenation of the alcohol substrate and catalyst independent stepwise attack of two equivalents of sulfone on the aldehyde under basic conditions. While the Ru(II) is only responsible for the initial dehydrogenation step, the rate of aldehyde formation is crucial to maintaining the right balance of intermediates needed to afford the cyclopropane product.

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