New regio-, stereo-, diastereo- and enantioselective one-pot reactions mediated by organometallic derivatives

2004 ◽  
Vol 76 (3) ◽  
pp. 517-535 ◽  
Author(s):  
Nicka Chinkov ◽  
G. Sklute ◽  
Helena Chechik ◽  
Adi Abramovitch ◽  
Deborah Amsallem ◽  
...  
Keyword(s):  
Double Bond ◽  
Asymmetric Synthesis ◽  
Potential Application ◽  
Bond Activation ◽  
Chiral Center ◽  
Elimination Reaction ◽  
One Pot ◽  
Carbon Carbon Bonds ◽  
New Strategy ◽  
The One

In the first part of the lecture, we will discuss the one-pot preparation of chiral homoallylic alcohol and amine derivatives by a copper-catalyzed four-component reaction. In this process, three new carbon-carbon bonds as well as a quaternary and a tertiary chiral center are created with excellent regio- and diastereoselectivities. When the reaction was performed without adding external electrophiles, a β-elimination reaction took place to give polysubstituted allenes in good overall yields. This strategy of zinc-homologation followed by a β-elimination reaction was also synthetically used for the transformation of sp3 sulfoxides into olefins with potential application in asymmetric synthesis. Finally, in the second part of this lecture, the stereoselective preparation of metallated dienes in only two chemical steps from commercially available products will be described. This new strategy is based on a tandem allylic C-H bond activation of a remote ω-double bond followed by an elimination reaction.

Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2523-2532 ◽  
Author(s):  
Long Zhao ◽  
Sun Li ◽  
Lei Wang ◽  
Shun Yu ◽  
Gerhard Raabe ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Domino Reactions ◽  
One Pot ◽  
New Strategy ◽  
The One

A new strategy for the N-heterocyclic carbene catalyzed asymmetric synthesis of cyclopentene-fused tetrahydroquinoline derivatives has been developed. The one-pot organocatalytic domino protocol allows a direct entry to the characteristic cyclopenta[c]tetrahydroquinoline core of many alkaloids and some potential drugs employing readily available quinolinone and enal substrates in good domino yields and stereoselectivities.

A New Strategy for the One Pot Synthesis of (Aryloxyimino)Ethylcoumarins Promoted by CuCl2

2012 ◽  
Vol 36 (1) ◽  
pp. 5-8 ◽  
Author(s):  
Gargi Pal ◽  
Pranabes Bhattacharyya ◽  
Arunima Medda ◽  
Asish R. Das
Keyword(s):  
One Pot ◽  
One Pot Synthesis ◽  
New Strategy ◽  
The One

The one pot asymmetric synthesis of 3,3′-pyrrolidonyl spiroxindoles via a regio- and stereoselective domino reaction

2019 ◽  
Vol 17 (35) ◽  
pp. 8140-8148
Author(s):  
Saumen Hajra ◽  
Suhas Shivajirao Bhosale ◽  
Atanu Hazra ◽  
Nikhil Kanaujia
Keyword(s):  
Asymmetric Synthesis ◽  
Domino Reaction ◽  
One Pot ◽  
The One

The asymmetric synthesis of 4-aryl-3,3′-spiropyrrolidonyl oxindoles with excellent stereoselectivity (dr >99 : 1 and an ee up to >99%) was achieved via a domino reaction.

A new strategy of spray pyrolysis to prepare porous carbon nanosheets with enhanced ionic sorption capacity

RSC Advances ◽  
2016 ◽  
Vol 6 (2) ◽  
pp. 1686-1693 ◽  
Author(s):  
Pung Ho Kim ◽  
Kyeong Youl Jung
Keyword(s):  
Spray Pyrolysis ◽  
Porous Carbon ◽  
Ultrasonic Spray Pyrolysis ◽  
One Pot ◽  
Carbon Nanosheets ◽  
Carbon Particles ◽  
Synthetic Strategy ◽  
New Strategy ◽  
Spray Pyrolysis Process ◽  
The One

We developed a new synthetic strategy to control the microstructure of carbon particles via ultrasonic spray pyrolysis. Porous carbon nanosheets with high ion-sorption capacitance were prepared by the one-pot spray pyrolysis process.

scholarly journals Ni-catalyzed deaminative cross-electrophile coupling of Katritzky salts with halides via C─N bond activation

2019 ◽  
Vol 5 (6) ◽  
pp. eaaw9516 ◽  
Author(s):  
Shengyang Ni ◽  
Chun-Xiao Li ◽  
Yu Mao ◽  
Jianlin Han ◽  
Yi Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Primary Amines ◽  
One Pot ◽  
Carbon Centers ◽  
Alkyl Bromides ◽  
Wide Range ◽  
Coupling Strategy ◽  
The One

The reductive cross-coupling of sp3-hybridized carbon centers represents great synthetic values and insurmountable challenges. In this work, we report a nickel-catalyzed deaminative cross-electrophile coupling reaction to construct C(sp)─C(sp3), C(sp2)─C(sp3), and C(sp3)─C(sp3) bonds. A wide range of coupling partners including aryl iodides, bromoalkynes, or alkyl bromides are stitched with alkylpyridinium salts that derived from the corresponding primary amines. The advantages of this methodology are showcased in the two-step synthesis of the key lactonic moiety of (+)-compactin and (+)-mevinolin. The one-pot procedure without isolation of alkylpyridinium tetrafluoroborate salt is also proven to be successful. This cross-coupling strategy of two electrophiles provides a highly valuable vista for the convenient installation of alkyl substituents and late functionalizations of sp3 carbons.

Ni-Catalyzed Deamination Cross-Electrophile Coupling of Katritzky Salts with Halides via C–N Bond Activation

2019 ◽  
Author(s):  
Shengyang Ni ◽  
Chunxiao Li ◽  
Jianlin Han ◽  
Yu Mao ◽  
Yi Pan
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Aryl Iodide ◽  
Cross Coupling Reaction ◽  
New Strategy ◽  
The Cross

This work describes the first Ni-catalyzed cross-electrophile coupling of alkylpyridinium salts, derived from the corresponding amines, with aryl iodide, bromoalkyne or bromoalkyl coupling partners. C(sp)-C(sp<sup>3</sup>), C(sp<sup>2</sup>)-C(sp<sup>3</sup>) and C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond formation was achieved to afford a variety of synthetically useful arenes, alkynes and alkanes in good yields from<b>2</b>-<b>33</b>. The advantages of the methodology are showcased in the two-step synthesis of the key lactonic moiety of (+)-Compactin and (+)-Mevinolin from commercially available starting materials. A one-pot procedure without isolation of alkylpyridinium tetrafluoroborate salt was also demonstrated to be successful. This work represents a new strategy for the cross-coupling reaction of two electrophiles, and also provides a complementary and highly valuable vista for the current methodologies of alkyl arene/alkyne/alkane synthesis.

An Efficient Synthesis of New 7-Trifluoromethyl-2,5-disubstituted Pyrazolo[1,5-a]pyrimidines

Synthesis ◽  
2018 ◽  
Vol 50 (08) ◽  
pp. 1675-1686 ◽  
Author(s):  
Mohamed Abarbri ◽  
Badr Jismy ◽  
Hassan Allouchi ◽  
Gérald Guillaumet ◽  
Mohamed Akssira
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Building Blocks ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
One Pot ◽  
One Pot Synthesis ◽  
Biological Interest ◽  
The One

A novel two-step synthesis of trifluoromethylated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines is reported from 3-aminopyrazoles and ethyl 4,4,4-trifluorobut-2-ynoate. The synthetic route begins with the one-pot synthesis of 7-trifluoromethylated pyrazolo[1,5-a]pyrimidin-5-ones by condensation of 3-aminopyrazoles with a fluorinated alkyne. The products obtained are used as building blocks to synthesize directly, with excellent yields via C–O bond activation, a library of new fluorinated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines of biological interest. This operation efficiently allows C–C, C–N and C–S bond formation.

Bench-stable imine surrogates for the one-pot and catalytic asymmetric synthesis of α-amino esters/ketones

2020 ◽  
Vol 56 (91) ◽  
pp. 14243-14246
Author(s):  
Huacheng Xu ◽  
Adila Nazli ◽  
Cheng Zou ◽  
Zhi-Peng Wang ◽  
Yun He
Keyword(s):  
Asymmetric Synthesis ◽  
One Pot ◽  
Amino Esters ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric ◽  
The One

An unpresented catalytic asymmetric method for the synthesis of α-amino esters and ketones from novel imine surrogates is reported.

scholarly journals Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis

2011 ◽  
Vol 7 ◽  
pp. 1315-1322 ◽  
Author(s):  
Inhee Cho ◽  
Labros Meimetis ◽  
Lee Belding ◽  
Michael J Katz ◽  
Travis Dudding ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Ligand ◽  
One Pot ◽  
Rapid Access ◽  
Short Synthesis ◽  
The One

A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxides serve as directed metalation groups. The optimization and scope of this reaction are discussed, and the utility of this process is demonstrated in the one-pot preparation of a number of chiral diols as well as a short synthesis of the chiral ligand Vivol.

A strategy for the one-pot synthesis of sialylated oligosaccharides

2002 ◽  
Vol 80 (8) ◽  
pp. 1051-1054 ◽  
Author(s):  
Zhiyuan Zhang ◽  
Kenichi Niikura ◽  
Xue-Fei Huang ◽  
Chi-Huey Wong
Keyword(s):  
Sialic Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
New Strategy ◽  
The One ◽  
Glycosyl Donors

A new strategy has been developed for the synthesis of branched sialylated oligosaccharides using one-pot technology. Sialyl donors are in general too weak in reactivity to be used as the first glycosyl donors in the one-pot synthesis. When sialic acid is linked to a different sugar such as galactose, the reactivity is, however, significantly enhanced and can be tuned to enable the one-pot synthesis. A combination of NIS–TfOH–AgOTf was used for activation of the thioglycosides to improve the glycosylation yield when a hindered acceptor was used, as illustrated in the one-pot assembly of sialylated hexasaccharide.Key words: one-pot synthesis, sialyl oligosaccharides, new activation.

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