Enantioselective Synthesis of [7]Helicene: Dramatic Effects of Olefin Additives and Aromatic Solvents in Asymmetric Olefin Metathesis | Zendy

Grandbois Alain | Zendy; Collins Shawn K. | Zendy

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Enantioselective Synthesis of [7]Helicene: Dramatic Effects of Olefin Additives and Aromatic Solvents in Asymmetric Olefin Metathesis

Author(s) -

Grandbois Alain,

Collins Shawn K.

Publication year - 2008

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200801033

Subject(s) - helicene , enantioselective synthesis , kinetic resolution , olefin fiber , olefin metathesis , chemistry , ring opening metathesis polymerisation , acyclic diene metathesis , metathesis , organic chemistry , carbene , catalysis , molecule , polymerization , polymer

The asymmetric synthesis of [7]helicene was accomplished in good ee (80 %) by kinetic resolution by means of asymmetric olefin metathesis. Three key factors contributed to the success of the kinetic resolution: the use of new Ru‐based olefin metathesis catalysts bearing C 1 ‐symmetric N‐heterocyclic carbene ligands, simple olefins as additives to control the nature of the propagating alkylidene and hexafluorobenzene as a solvent.

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