Generation and Conjugate Additions ofo-Quinone Methides Under Mild Base Conditions: Rapid Synthesis ofN-Substituted Aryl Glycine Derivatives

2013 ◽  
Vol 2013 (36) ◽  
pp. 8299-8306 ◽  
Author(s):  
Wei Wang ◽  
Zhong Zheng ◽  
Xiangmin Wang ◽  
Jinchun Chen
Keyword(s):  
Quinone Methides ◽  
Rapid Synthesis ◽  
Conjugate Additions ◽  
Glycine Derivatives

Non-hydrogen bond catalyst-mediated diastereoselective conjugate additions of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides

2020 ◽  
Vol 18 (35) ◽  
pp. 6807-6811
Author(s):  
Ziyang Wang ◽  
Anqi Huang ◽  
Fang Fang ◽  
Pengfei Li ◽  
Guokai Liu ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Conjugate Additions ◽  
High Yields

An efficient DBU-catalyzed conjugate addition of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides has been developed, affording the valuable diarylmethanes in high yields with excellent diastereoselectivity.

Formal [4 + 1] cycloaddition of o-quinone methides: facile synthesis of dihydrobenzofurans

RSC Advances ◽  
2015 ◽  
Vol 5 (20) ◽  
pp. 14953-14957 ◽  
Author(s):  
Xiantao Lei ◽  
Chun-Huan Jiang ◽  
Xiaoan Wen ◽  
Qing-Long Xu ◽  
Hongbin Sun
Keyword(s):  
Facile Synthesis ◽  
Quinone Methides ◽  
Rapid Synthesis ◽  
Sulfur Ylides ◽  
Straightforward Method

An efficient and straightforward method for the rapid synthesis of 2-substituted dihydrobenzofurans has been developed via reaction of sulfur ylides with o-quinone methides (o-QMs).

Visible light-induced aerobic oxidative cross-coupling of glycine derivatives with indoles: a facile access to 3,3′ bisindolylmethanes

2018 ◽  
Vol 5 (13) ◽  
pp. 2120-2125 ◽  
Author(s):  
Yuan Zhang ◽  
Xiaorong Yang ◽  
Huang Zhou ◽  
Shilin Li ◽  
Yin Zhu ◽  
...  
Keyword(s):  
Visible Light ◽  
Cross Coupling ◽  
Alkylation Reaction ◽  
Rapid Synthesis ◽  
Glycine Derivatives

A rapid synthesis of 3,3′-bisindolylmethanes is achieved via a photocatalyzed double Friedel–Crafts alkylation reaction between glycine derivatives and indoles.

scholarly journals A formal intermolecular [4 + 1] cycloaddition reaction of 3-chlorooxindole and o-quinone methides: a facile synthesis of spirocyclic oxindole scaffolds

RSC Advances ◽  
2021 ◽  
Vol 11 (30) ◽  
pp. 18576-18579
Author(s):  
Chao Lin ◽  
Qi Xing ◽  
Honglei Xie
Keyword(s):  
Cycloaddition Reaction ◽  
Cyclization Reaction ◽  
Facile Synthesis ◽  
Quinone Methides ◽  
Rapid Synthesis ◽  
Mild Conditions ◽  
Straightforward Method ◽  
Spirocyclic Oxindole

Herein, we developed an efficient and straightforward method for the rapid synthesis of spirocyclic oxindole scaffolds via the [4 + 1] cyclization reaction of 3-chlorooxindole with o-quinone methides (o-QMs), which were generated under mild conditions.

Construction of fully substituted carbon centers containing a heteroatom and a CF3 group via in situ generated p-quinone methides

2021 ◽  
Vol 19 (6) ◽  
pp. 1305-1314
Author(s):  
Kyu Terashima ◽  
Tomoko Kawasaki-Takasuka ◽  
Takashi Yamazaki
Keyword(s):  
Quinone Methides ◽  
Conjugate Additions ◽  
Carbon Centers

Facile and practical construction of heteroatom as well as CF3-containing fully substituted carbon centers was realized by 1,6-conjugate additions of a variety of heteronucleophiles to in situ generated δ-CF3-δ-substituted p-quinone methides.

Base-Mediated Tandem 1,6-Addition/Cyclization/Isomerization Reactions between para-Quinone Methides and Benzyl Chlorides: Approaches to Diverse Frameworks at Each Cascade Stage

Synthesis ◽  
2019 ◽  
Vol 51 (10) ◽  
pp. 2136-2148 ◽  
Author(s):  
Shangkun Zhao ◽  
Yuanyuan Zhu ◽  
Minli Zhang ◽  
Xixi Song ◽  
Junbiao Chang
Keyword(s):  
Single Step ◽  
Tandem Reactions ◽  
Cesium Carbonate ◽  
Cyclization Reactions ◽  
Quinone Methides ◽  
Conjugate Additions ◽  
Benzyl Chlorides

Base-mediated stereospecific tandem reactions using para-quinone methides and carbene-like benzyl chlorides are developed. DBU-mediated 1,6-addition/cyclization/isomerization reactions produce triarylsubstituted alkenes in 43–89% yields and Z/E ratios of 5:1 to 35:1 in favor of the Z-isomers. Single-step 1,6-conjugate additions are realized with the mediation of cesium carbonate, and different triaryl chloroethanes are obtained in yields of 41–54% and excellent diastereoselectivities of more than 20:1. In addition, tandem 1,6-addition/cyclization reactions are achieved using tuned 2,4-disubstituted benzyl chlorides to afford diaryl spirocyclopropyl para-dienones in yields of 35–83% and diastereoselectivities of more than 20:1 in favor of the anti-isomers. The transformations from triaryl chloroethanes and spirocyclopropyl para-dienones into triarylsubstituted alkenes are also demonstrated to support the proposed tandem mechanisms.

Syntheses of α-CF3-α-quaternary ketones via p-quinone methides and their derivatization to compounds with successively congested stereogenic centers

2020 ◽  
Vol 18 (24) ◽  
pp. 4638-4644 ◽  
Author(s):  
Kyu Terashima ◽  
Tomoko Kawasaki-Takasuka ◽  
Tomohiro Agou ◽  
Toshio Kubota ◽  
Takashi Yamazaki
Keyword(s):  
Quinone Methides ◽  
Conjugate Additions ◽  
Stereogenic Centers

NHC-catalyzed 1,6-conjugate additions of a variety of aldehydes to δ-CF3-δ-substituted p-quinone methides and their highly diastereoselective derivatization to compounds with successively congested stereogenic centers were performed.

Modified Solid-Phase Methods for the Rapid Synthesis of Opioid Peptides

1991 ◽  
Author(s):  
Richard A. Houghten ◽  
◽  
John M. Ostresh ◽  
Suzanne M. Pratt
Keyword(s):  
Opioid Peptides ◽  
Solid Phase ◽  
Rapid Synthesis

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

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