Enantioselective synthesis of seven-membered carbo- and heterocyles by organocatalyzed intramolecular Michael addition

Enantioenriched seven membered rings have been prepared in high yields and stereoselectivities by intramolecular Michael addition of functionalized enals catalyzed by Jorgensen–Hayashi catalyst.

Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones

Zeitschrift für Naturforschung B ◽

10.5560/znb.2012-0183 ◽

2012 ◽

Vol 67 (10) ◽

pp. 1021-1029 ◽

Cited By ~ 9

Author(s):

Magnus Rueping ◽

Stefan A. Moreth ◽

Michael Bolte

Keyword(s):

Michael Addition ◽

Heterocyclic Compounds ◽

Michael Reaction ◽

Biological Activities ◽

Bronsted Acid ◽

Brønsted Acid ◽

Brönsted Acid ◽

Acid Catalyzed ◽

The enantioselective synthesis of 2-aryl-substituted 2,3-dihydroquinolin-4-ones, a class of heterocyclic compounds with interesting biological activities, has been achieved through a Brønsted acidcatalyzed enantioselective intramolecular Michael addition. The products are available in moderate to high yields and with good enantioselectivities.

Enantioselective synthesis of chiral α,β-unsaturated γ-substituted butyrolactams by organocatalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines

Organic & Biomolecular Chemistry ◽

10.1039/c6ob01191h ◽

2016 ◽

Vol 14 (27) ◽

pp. 6568-6576 ◽

Cited By ~ 21

Author(s):

Zhen-Hua Wang ◽

Zhi-Jun Wu ◽

Deng-Feng Yue ◽

Yong You ◽

Xiao-Ying Xu ◽

...

Keyword(s):

Michael Addition ◽

Optically Active ◽

Approach providing a series of optically active α,β-unsaturated γ-substituted butyrolactams in high yields with excellent diastereo- and enantioselectivities.

Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition

Organic & Biomolecular Chemistry ◽

10.1039/c4ob01646g ◽

2014 ◽

Vol 12 (43) ◽

pp. 8607-8610 ◽

Cited By ~ 13

Author(s):

Shuanghua Cheng ◽

Shouyun Yu

Keyword(s):

Michael Addition ◽

A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er).

Lithiated three-membered heterocycles as chiral nucleophiles in the enantioselective synthesis of 1-oxaspiro[2,3]hexanes

Organic & Biomolecular Chemistry ◽

10.1039/d0ob00771d ◽

2021 ◽

Author(s):

Andrea Cocco ◽

Maria Grazia Rubanu ◽

Maria Laura Sechi ◽

Angelo Frongia ◽

Pietro Mastrorilli ◽

...

Keyword(s):

Styrene Oxide ◽

Enantiomerically enriched oxaspiro- and azaspirohexanes were synthesized through a two-step addition of configurably stable Li-styrene oxide (or aziridine) to 3-substituted cyclobutanones and base-mediated Payne rearrangement sequence with high yields and selectivity.

ChemInform Abstract: Diastereo- and Enantioselective Synthesis of Densely Functionalized Cyclohexanones via Double Michael Addition of Curcumins with Nitroalkenes.

ChemInform ◽

10.1002/chin.201246095 ◽

2012 ◽

Vol 43 (46) ◽

pp. no-no

Author(s):

Narasimham Ayyagari ◽

Irishi N. N. Namboothiri

Keyword(s):

Michael Addition ◽

Enantioselective Synthesis

ChemInform Abstract: The Efficient Enantioselective Synthesis of Dihydropyrans via Organocatalytic Michael Addition Reactions.

ChemInform ◽

10.1002/chin.201450023 ◽

2014 ◽

Vol 45 (50) ◽

pp. no-no

Author(s):

Zhiqiang Niu ◽

Xinwei He ◽

Yongjia Shang

Keyword(s):

Michael Addition ◽

Addition Reactions

ChemInform Abstract: Highly Enantioselective Synthesis of α-Fluoro-α-nitro Esters via Organocatalyzed Asymmetric Michael Addition.

ChemInform ◽

10.1002/chin.201116056 ◽

2011 ◽

Vol 42 (16) ◽

pp. no-no

Author(s):

Hai-Feng Cui ◽

Peng Li ◽

Xiao-Wei Wang ◽

Zhuo Chai ◽

Ying-Quan Yang ◽

...

Keyword(s):

Michael Addition ◽

Asymmetric Michael Addition ◽

Nitro Esters

Enantioselective Synthesis of Quaternary 3-Aminooxindoles via Organocatalytic Asymmetric Michael Addition of 3-Monosubstituted 3-Aminooxindoles to Nitroolefins

The Journal of Organic Chemistry ◽

10.1021/jo401154b ◽

2013 ◽

Vol 78 (17) ◽

pp. 8833-8839 ◽

Cited By ~ 50

Author(s):

Bao-Dong Cui ◽

Wen-Yong Han ◽

Zhi-Jun Wu ◽

Xiao-Mei Zhang ◽

Wei-Cheng Yuan

Keyword(s):

Michael Addition ◽

Asymmetric Michael Addition

Catalytic Enantioselective Synthesis of Chiral Spirocyclic 1,3-Diketones via Organo-Cation Catalysis

Chemical Communications ◽

10.1039/d1cc05205e ◽

2021 ◽

Author(s):

Xiao-Yan Zhang ◽

Ya-Ping Shao ◽

Bao-Kuan Guo ◽

Kun Zhang ◽

Fu-Min Zhang ◽

...

Keyword(s):

High Yields ◽

Convenient Access

An SPA-triazolium bromide catalyzed transannular C-acylation of enol lactones is presented. This methodology provides convenient access to a range of enantioenriched spirocyclic 1,3-diketones in moderate to high yields and enantioselectivities...

Facile Synthesis of 2-Arylindoles through Plancher-Type Rearrangement of 3-Alkyl-3-Arylindolenines

Synlett ◽

10.1055/s-0036-1588448 ◽

2017 ◽

Vol 28 (15) ◽

pp. 1994-1999

Author(s):

Santhosh Chittimalla ◽

Chennakesavulu Bandi ◽

Vinod Gadi ◽

Siva Gunturu

Keyword(s):

Michael Addition ◽

Facile Synthesis ◽

Type C ◽

3-Alkylindoles on reaction with a cyclohexa-2,4-dien-1-one catalyzed by BF3·OEt2 gave the corresponding 3-alkyl-3-arylindolenines in high yields through a tandem Michael addition/aromatization sequence. In the presence of HCl, these indolenine derivatives underwent a facile Plancher-type C-3 to C-2 aryl rearrangement to deliver the corresponding 2-arylindoles.