Expeditious assembly of fused dihydropyranones via N-heterocyclic carbene-catalyzed tandem Michael addition/lactonization

2017 ◽  
Vol 15 (6) ◽  
pp. 1329-1333 ◽  
Author(s):  
Qiao Ren ◽  
Muyao Li ◽  
Lujiang Yuan
Keyword(s):  
Michael Addition ◽  
Optically Active ◽  
High Yields

A convergent and efficient NHC-catalyzed enantioselective tandem Michael addition/lactonization sequence of ynals with 1,2-dione is disclosed. This strategy expeditiously assembles the valuable optically active fused dihydropyranones in good to high yields and with excellent 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

2016 ◽  
Vol 14 (27) ◽  
pp. 6568-6576 ◽  
Author(s):  
Zhen-Hua Wang ◽  
Zhi-Jun Wu ◽  
Deng-Feng Yue ◽  
Yong You ◽  
Xiao-Ying Xu ◽  
...  
Keyword(s):  
Michael Addition ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
High Yields

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

Formation of Optically Active Chromans by Catalytic Asymmetric Tandem Oxa-Michael Addition—Friedel—Crafts Alkylation Reactions.

ChemInform ◽  
2003 ◽  
Vol 34 (39) ◽  
Author(s):  
Hester L. van Lingen ◽  
Wei Zhuang ◽  
Tore Hansen ◽  
Floris P. J. T. Rutjes ◽  
Karl Anker Joergensen
Keyword(s):  
Michael Addition ◽  
Optically Active ◽  
Catalytic Asymmetric ◽  
Alkylation Reactions

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

RSC Advances ◽  
2016 ◽  
Vol 6 (36) ◽  
pp. 30166-30169 ◽  
Author(s):  
James O. Guevara-Pulido ◽  
José M. Andrés ◽  
Deisy P. Ávila ◽  
Rafael Pedrosa
Keyword(s):  
Michael Addition ◽  
Enantioselective Synthesis ◽  
High Yields

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

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

Synlett ◽  
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 ◽  
High Yields

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.

Synthesis of 4-arylethyl-6-arylpyrimidine-2-thiols through aza-Michael addition/nucleophilic addition/aromatization tandem reactions

2018 ◽  
Vol 24 (1) ◽  
pp. 23-26
Author(s):  
Zheng Li ◽  
Wenli Song ◽  
Jiaojiao He ◽  
Yan Du ◽  
Jingya Yang
Keyword(s):  
Efficient Method ◽  
Michael Addition ◽  
Nucleophilic Addition ◽  
Tandem Reactions ◽  
Reaction Conditions ◽  
High Yields ◽  
Work Up

Abstract An efficient method for the synthesis of the title compounds by reactions of divinyl ketones with thiourea is described. This protocol has the advantages of high yields, mild reaction conditions and simple work-up procedure.

Asymmetric α-Amination Reaction of Alkenoate Cyclic Esters Catalyzed by Chiral Tin Alkoxides

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 738-742
Author(s):  
Akira Yanagisawa ◽  
Yoshiki Yamashita ◽  
Chika Uchiyama ◽  
Ryuta Nakano ◽  
Moe Horiguchi ◽  
...  
Keyword(s):  
Optically Active ◽  
Cyclic Esters ◽  
Amination Reaction ◽  
High Yields ◽  
Sodium Alkoxide

A catalytic enantioselective α-amination reaction of alkenoate cyclic esters with dialkyl azodicarboxylates was achieved by using a 3,3′-di(1-naphthyl)-substituted (R)-BINOL–dibromostannane complex as a chiral precatalyst in the presence of a sodium alkoxide and an alcohol. Optically active α-hydrazino ketones were obtained in moderate to high yields and with up to 91% ee in the presence of the chiral tin alkoxide generated in situ.

scholarly journals Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts

2012 ◽  
Vol 8 ◽  
pp. 699-704 ◽  
Author(s):  
Saet Byeol Woo ◽  
Dae Young Kim
Keyword(s):  
Michael Addition ◽  
Catalyst Loading ◽  
High Yields ◽  
Low Catalyst Loading

The highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes, promoted by binaphthyl-modified chiral bifunctional organocatalysts is described. This reaction afforded the chiral functionalized naphthoquinones in high yields (81–95%) and excellent enantioselectivities (91–98% ee) under low catalyst loading (1 mol %).

Catalytic asymmetric addition reactions leading to carbon-carbon bond formation: Phenyl and alkenyl transfer to aldehydes and alkynylation of α-imino esters

2006 ◽  
Vol 78 (2) ◽  
pp. 267-274 ◽  
Author(s):  
Jian-Xin Ji ◽  
Jing Wu ◽  
Lijin Xu ◽  
Chiu-Wing Yip ◽  
Kim Hung Lam ◽  
...  
Keyword(s):  
Bond Formation ◽  
Optically Active ◽  
Amino Acid Derivatives ◽  
Addition Reactions ◽  
Terminal Alkynes ◽  
Reaction Conditions ◽  
Carbon Carbon Bond ◽  
Catalytic Asymmetric ◽  
High Yields ◽  
Imino Esters

Optically active tertiary aminonaphthol ligands were obtained by a new, convenient procedure and were found to catalyze the enantioselective alkenyl and phenyl transfer to aldehydes in high yields and excellent enantiomeric excesses (ee's). The catalytic asymmetric introduction of alkynyl functionality to α-amino acid derivatives was realized by the direct addition of terminal alkynes to α-imino ester in the presence of chiral copper(I) complex under mild reaction conditions.

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