Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy | Zendy

Rosa M. Girón | Zendy; Jiangkun Ouyang | Zendy; Ludovic Favereau | Zendy; Nicolas Vanthuyne | Zendy; Jeanne Crassous | Zendy; Salvatore Filippone | Zendy; Nazario Martı́n | Zendy

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Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy

Author(s) -

Rosa M. Girón,

Jiangkun Ouyang,

Ludovic Favereau,

Nicolas Vanthuyne,

Jeanne Crassous,

Salvatore Filippone,

Nazario Martı́n

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b00256

Subject(s) - helicene , diastereomer , chemistry , cycloaddition , fullerene , enantioselective synthesis , resolution (logic) , 1,3 dipolar cycloaddition , catalysis , combinatorial chemistry , organic chemistry , molecule , artificial intelligence , computer science

[60]Fullerene and its rarely explored reversible covalent chemistry have been harnessed as an efficient alternative for the chiral resolution of racemates. By using only catalytic amounts of chiral agents, stereodivergent 1,3-dipolar cycloadditions of racemic helicenes onto [60]fullerene were carried out. The formed helicene/fullerene diastereomers were easily separated by conventional chromatography, and afterward, a simple catalyzed 1,3-dipolar retro-cycloaddition afforded helicene starting materials in high optical purity.

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