Copper(ii)/amine synergistically catalyzed enantioselective alkylation of cyclic N-acyl hemiaminals with aldehydes

A copper/amine synergistic catalytic system was developed, allowing the first catalytic asymmetric alkylation of N-acyl quinoliniums with aldehydes in high yields and excellent enantioselectivities.

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Copper-catalyzed 1,6-conjugate addition of para-quinone methides with diborylmethane

Organic Chemistry Frontiers ◽

10.1039/d1qo00632k ◽

2021 ◽

Author(s):

Xin Li ◽

Guoliang Gao ◽

Songtao He ◽

Qiuling Song

Keyword(s):

Catalytic System ◽

Conjugate Addition ◽

Quinone Methides ◽

High Yields

Presented herein is the first 1,6-conjugate addition of diborylmethane, which is promoted by a simple and inexpensive copper catalytic system. This method features high yields, good selectivities and broad functional...

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Catalytic, asymmetric alkylation of imines

Tetrahedron ◽

10.1016/j.tet.2007.06.043 ◽

2007 ◽

Vol 63 (39) ◽

pp. 9581-9597 ◽

Cited By ~ 67

Author(s):

Dana Ferraris∗

Keyword(s):

Asymmetric Alkylation ◽

Catalytic Asymmetric

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ChemInform Abstract: Catalytic Asymmetric Synthesis of Chiral 4-Pyrazolylalkanols by the Enantioselective Alkylation of Pyrazole-4-carbaldehydes with Dialkylzincs.

ChemInform ◽

10.1002/chin.200017124 ◽

2010 ◽

Vol 31 (17) ◽

pp. no-no

Author(s):

Shigehisa Tanji ◽

Harumi Aoyagi ◽

Hayami Tabira ◽

Itaru Sato ◽

Kenso Soai

Keyword(s):

Asymmetric Synthesis ◽

Catalytic Asymmetric Synthesis ◽

Catalytic Asymmetric ◽

Enantioselective Alkylation

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Catalytic asymmetric C2-nucleophilic substitutions of C3-substituted indoles with ortho-hydroxybenzyl alcohols

Organic Chemistry Frontiers ◽

10.1039/c7qo00649g ◽

2017 ◽

Vol 4 (12) ◽

pp. 2465-2479 ◽

Cited By ~ 26

Author(s):

Jia-Le Wu ◽

Jing-Yi Wang ◽

Ping Wu ◽

Guang-Jian Mei ◽

Feng Shi

Keyword(s):

Nucleophilic Substitutions ◽

Catalytic Asymmetric ◽

High Yields

Catalytic asymmetric C2-nucleophilic substitutions of C3-substituted indoles such as tryptophols or tryptamines with ortho-hydroxybenzyl alcohols have been established, leading to the generation of triaryl methane products in generally high yields and excellent enantioselectivities.

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Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with ortho-Quinone Methides

Molecules ◽

10.3390/molecules26216751 ◽

2021 ◽

Vol 26 (21) ◽

pp. 6751

Author(s):

Si-Jia Liu ◽

Man-Su Tu ◽

Kai-Yue Liu ◽

Jia-Yi Chen ◽

Shao-Fei Ni ◽

...

Keyword(s):

Phosphoric Acid ◽

Structural Diversity ◽

Quinone Methides ◽

Chiral Phosphoric Acid ◽

Catalytic Asymmetric ◽

High Yields ◽

Asymmetric Cycloadditions

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.

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Catalytic Asymmetric Substitution Reaction of 3-Substituted 2-Indolylmethanols with 2-Naphthols

Synthesis ◽

10.1055/s-0040-1707237 ◽

2020 ◽

Vol 52 (23) ◽

pp. 3684-3692

Author(s):

Feng Gao ◽

Yu-Chen Zhang ◽

Feng Shi ◽

Jin-Ping Lan ◽

Yi-Nan Lu ◽

...

Keyword(s):

Phosphoric Acid ◽

Substitution Reaction ◽

Enantioselective Synthesis ◽

Chiral Phosphoric Acid ◽

Catalytic Asymmetric ◽

High Yields

A catalytic asymmetric substitution of 3-substituted 2-indolylmethanols with 2-naphthols has been established under the catalysis of chiral phosphoric acid. By this approach, a series of structurally diversified triarylmethane derivatives were obtained in moderate to high yields with good enantioselectivities (up to 97% yield, 95:5 er). This approach not only enriches the chemistry of 2-indolylmethanol-inolved catalytic asymmetric substitutions, but also provides a useful method for the enantioselective synthesis of chiral triarylmethane derivatives.

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