Rhodium Catalysts with a Chiral Cyclopentadienyl Ligand Derived from Natural R‐Myrtenal | Zendy

Pototskiy Roman A. | Zendy; Kolos Andrey V. | Zendy; Nelyubina Yulia V. | Zendy; Perekalin Dmitry S. | Zendy

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Rhodium Catalysts with a Chiral Cyclopentadienyl Ligand Derived from Natural R‐Myrtenal

Author(s) -

Pototskiy Roman A.,

Kolos Andrey V.,

Nelyubina Yulia V.,

Perekalin Dmitry S.

Publication year - 2020

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202001029

Subject(s) - chemistry , rhodium , myr , cyclopentadienyl complex , medicinal chemistry , enantioselective synthesis , ligand (biochemistry) , catalysis , yield (engineering) , total synthesis , derivative (finance) , organic chemistry , stereochemistry , biochemistry , receptor , materials science , genome , economics , financial economics , metallurgy , gene

A new chiral cyclopentadiene Cp myr H was synthesized from the natural terpene ( R )‐myrtenal in 5 steps and about 40 % total yield. The key step was the reaction of vinyl‐dibromocyclopropane derivative with MeLi which provided the diene Cp myr H via Skattebøl rearrangement. The reaction of Cp myr H with [(cod)Rh(OAc)] 2 gave the rhodium(I) complex (Cp myr )Rh(cod) and subsequent oxidation with halogens X 2 gave the rhodium(III) complexes [(Cp myr )RhX 2 ] 2 (X = Br, I). Complex (Cp myr )Rh(cod) in combination with benzoyl peroxide catalyzed the C–H activation of O ‐pivaloyl‐phenylhydroxamic acid and its subsequent annulation with alkenes giving dihydroisoquinolones with high yield (70–90 %) but moderate enantioselectivity (16–36 % ee ).

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