One‐Pot Enantioselective Synthesis of 1,4‐Naphthoquinone‐Derived Polycycles through Oxidative Dearomatization and Aminocatalysis | Zendy

Pantaine Loïc | Zendy; Coeffard Vincent | Zendy; Moreau Xavier | Zendy; Greck Christine | Zendy

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One‐Pot Enantioselective Synthesis of 1,4‐Naphthoquinone‐Derived Polycycles through Oxidative Dearomatization and Aminocatalysis

Author(s) -

Pantaine Loïc,

Coeffard Vincent,

Moreau Xavier,

Greck Christine

Publication year - 2015

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.201403597

Subject(s) - chemistry , enantioselective synthesis , cycloaddition , oxidative phosphorylation , naphthoquinone , enantiomer , catalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , biochemistry

A synthetic process merging oxidative dearomatization and asymmetric aminocatalysis in a single vessel is reported. The PhI(OAc) 2 ‐mediated oxidation of 1,4‐dihydroxynaphthalene is followed by a trienamine‐mediated Diels–Alder cycloaddition/aldol reaction or a trienamine‐mediated Diels–Alder cycloaddition/oxidation sequence depending on the dienal substitution pattern. The polycyclic compounds are obtained in good yields with enantiomeric excesses up to 99 %. Additionally, these polycyclic architectures can be synthesized with similar enantioselectivities through an unprecedented one‐pot marriage of bodipy‐photocatalyzed oxidative dearomatization of 1‐naphthol and asymmetric aminocatalysis. A catalytic cycle is suggested to explain the reaction outcome.

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