- Regio- A nd Enantioselective Friedel-Crafts Benzhydrylation of Indoles in Carbocyclic Ring with ortho-Quinomethanes: Access to Chiral Diarylindolylmethanes
-
The functionalization of indoles in the carbocyclic ring has been achieved via organocatalytic enantioselective Friedel-Crafts benzhydrylation of hydroxyindoles with in situ generated ortho-quinomethanes in oil-water biphases, allowing an efficient access to varied diarylindolylmethanes with a wide substrate scope. The high yields, excellent stereoselectivities, mild conditions, low catalyst loading, and easy scalability also demonstrated the interest of this novel methodology.
- Chu, Ming-Ming,Chen, Xue-Yang,Wang, Yi-Feng,Qi, Suo-Suo,Jiang, Zhen-Hui,Xu, Dan-Qian,Xu, Zhen-Yuan
-
p. 9491 - 9502
(2020/09/03)
-
- A base-promoted cascade reaction of α,β-unsaturated: N -tosylhydrazones with o -hydroxybenzyl alcohols: Highly regioselective synthesis of N-sec -alkylpyrazoles
-
An efficient method for the synthesis of N-sec-alkylpyrazoles through a base-promoted cascade cyclization/Michael addition reaction of α,β-unsaturated N-tosylhydrazones with ortho-hydroxybenzyl alcohols has been developed. The desired products containing di- or triaryl groups at the same carbon atom were afforded in good to excellent yields with excellent regioselectivities (>20:1). Moreover, a three-component reaction of ortho-hydroxybenzyl alcohols, α,β-unsaturated N-tosylhydrazones and saturated N-tosylhydrazones also took place to afford pyrazoles in good yields. This reaction offers a new route to triarylmethanes with a simple operation and is applicable for large-scale synthesis.
- Chen, Lian-Mei,Zhao, Juan,Xia, An-Jie,Guo, Xiao-Qiang,Gan, Ya,Zhou, Chuang,Yang, Zai-Jun,Yang, Jun,Kang, Tai-Ran
-
supporting information
p. 8561 - 8570
(2019/10/02)
-
- Synthesis of chiral pyrazolone and spiropyrazolone derivatives through squaramide-catalyzed reaction of pyrazolin-5-ones with o-quinone methides
-
A bifunctional squaramide-catalyzed reaction of pyrazolin-5-ones with o-quinone methides in situ generated from 2-(1-tosylalkyl)phenols has been successfully developed, providing a facile access to chiral pyrazolones with high enantioselectivities. In addition, the chiral spiropyrazolones with adjacent tertiary and quaternary stereogenic centers can also be obtained through cascade chlorination/cyclization of the chiral pyrazolones.
- Zhou, Ji,Huang, Wen-Jun,Jiang, Guo-Fang
-
supporting information
p. 1158 - 1161
(2018/02/23)
-
- Bifunctional squaramide-catalyzed synthesis of chiral dihydrocoumarins via ortho-quinone methides generated from 2-(1-tosylalkyl)phenols
-
A bifunctional squaramide-catalyzed reaction of azlactones with o-quinone methides in situ generated from 2-(1-tosylalkyl)-phenols has been successfully developed under basic conditions, providing an efficient and mild access to chiral dihydrocoumarins bearing adjacent tertiary and quaternary stereogenic centers in high yields with excellent diastereo- and enantioselectivities.
- Zhou, Ji,Wang, Mao-Lin,Gao, Xiang,Jiang, Guo-Fang,Zhou, Yong-Gui
-
supporting information
p. 3531 - 3534
(2017/03/30)
-
- Bifunctional Amine-Squaramide Catalyzed Friedel–Crafts Alkylation Based on ortho-Quinone Methides in Oil-Water Phases: Enantioselective Synthesis of Triarylmethanes
-
An efficient enantioselective Friedel–Crafts alkylation reaction of electron-rich β-naphthol with in situ generated ortho-quinone methides catalyzed by chiral bifunctional amine-squaramide catalysts has been developed. The chiral triarylmethane derivative
- Wang, Yifeng,Zhang, Cheng,Wang, Haojiang,Jiang, Yidong,Du, Xiaohua,Xu, Danqian
-
supporting information
p. 791 - 797
(2017/03/11)
-
- Regioselective α-Addition of Deconjugated Butenolides: Enantioselective Synthesis of Dihydrocoumarins
-
The enantioselective α-addition of deconjugated butenolides has rarely been exploited, in contrast to the well-studied γ-addition of deconjugated butenolides. In this study, an unprecedented asymmetric α-addition/transesterification of deconjugated butenolides with ortho-quinone methides generated in situ afforded a series of functionalized 3,4-dihydrocoumarins containing two contiguous stereogenic centers with excellent diastereo- and enantioselectivity. DFT calculations suggested that the rarely observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic dienolate and the electrophilic ortho-quinone methide.
- Wu, Bo,Yu, Zhaoyuan,Gao, Xiang,Lan, Yu,Zhou, Yong-Gui
-
supporting information
p. 4006 - 4010
(2017/03/27)
-
- Enantioselective synthesis of functionalized 2-amino-4H-chromenes via the o-quinone methides generated from 2-(1-tosylalkyl)phenols
-
An efficient bifunctional squaramide-catalyzed Michael addition/cyclization reaction of o-quinone methides generated in situ from 2-(1-tosylalkyl)phenols with active methylene compounds bearing a cyano group has been realized to synthesize chiral 2-amino-
- Wu, Bo,Gao, Xiang,Yan, Zhong,Huang, Wen-Xue,Zhou, Yong-Gui
-
p. 4334 - 4338
(2015/06/22)
-
- A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o-Quinone Methides Generated from 2-(1-Tosylalkyl)phenols
-
A concise synthesis of 2-(2-hydroxyphenyl)acetonitriles has been developed through reaction of trimethylsilyl cyanide and the o-quinone methides in situ generated from 2-(1-tosylalkyl)phenols under basic conditions. In addition, 2-(2-hydroxyphenyl)acetonitriles could be conveniently transformed to benzofuranones.
- Wu, Bo,Gao, Xiang,Chen, Mu-Wang,Zhou, Yong-Gui
-
supporting information
p. 981 - 984
(2016/02/18)
-
- A mild method for generation of o-quinone methides under basic conditions. the facile synthesis of trans-2,3-dihydrobenzofurans
-
A novel and efficient method for the generation of o-quinone methide intermediates was developed from the readily available 2-tosylalkylphenols under the mild basic conditions, and their reactions with sulfur ylides were investigated for the stereoselective synthesis of trans-2,3-dihydrobenzofurans. The Royal Society of Chemistry 2013.
- Chen, Mu-Wang,Cao, Liang-Liang,Ye, Zhi-Shi,Jiang, Guo-Fang,Zhou, Yong-Gui
-
supporting information
p. 1660 - 1662
(2013/03/14)
-
- Synthesis of fluorenone derivatives through Pd-catalyzed dehydrogenative cyclization
-
Palladium-catalyzed dual C-H functionalization of benzophenones to form fluorenones by oxidative dehydrogenative cyclization is reported. This method provides a concise and effective route toward the synthesis of fluorenone derivatives, which shows outstanding functional group compatibility.
- Li, Hu,Zhu, Ru-Yi,Shi, Wen-Juan,He, Ke-Han,Shi, Zhang-Jie
-
supporting information
p. 4850 - 4853,4
(2012/12/12)
-
- Enantioselective addition of boronates to o -quinone methides catalyzed by chiral biphenols
-
Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the pr
- Luan, Yi,Schaus, Scott E.
-
supporting information
p. 19965 - 19968
(2013/02/22)
-