Synthesis of Carbo[6]helicene Derivatives Grafted with Amino or Aminoester Substituents from Enantiopure [6]Helicenyl Boronates | Zendy

Nora Hellou | Zendy; Aurélie Macé | Zendy; Clothilde Martin | Zendy; Vincent Dorcet | Zendy; Thierry Roisnel | Zendy; Marion Jean | Zendy; Nicolas Vanthuyne | Zendy; Fabienne Berrée | Zendy; Bertrand Carboni | Zendy; Jeanne Crassous | Zendy

Open Access

Synthesis of Carbo[6]helicene Derivatives Grafted with Amino or Aminoester Substituents from Enantiopure [6]Helicenyl Boronates

Author(s) -

Nora Hellou,

Aurélie Macé,

Clothilde Martin,

Vincent Dorcet,

Thierry Roisnel,

Marion Jean,

Nicolas Vanthuyne,

Fabienne Berrée,

Bertrand Carboni,

Jeanne Crassous

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b02619

Subject(s) - enantiopure drug , chemistry , reductive amination , alkylation , morpholine , helicene , chirality (physics) , amination , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , molecule , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model

Enantiopure carbo[6]helicenyl boronates were synthesized using a photocyclization reaction as the key step. These compounds were further converted to various amino derivatives using copper-catalyzed azidation or amination and reductive alkylation of benzylazide by a helicenyl dichloroborane. Asymmetric Petasis condensation with glyoxylic acid and morpholine controlled by the helical chirality afforded the corresponding amino esters.

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