Highly Selective Three‐Step Synthesis of Rhein in Chloroaluminate Molten Salt: Preclusion of the Hayashi Rearrangement | Zendy

Gonnot Vanessa | Zendy; Antheaume Cyril | Zendy; Nicolas Marc | Zendy; Mioskowski Charles | Zendy; Baati Rachid | Zendy

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Highly Selective Three‐Step Synthesis of Rhein in Chloroaluminate Molten Salt: Preclusion of the Hayashi Rearrangement

Author(s) -

Gonnot Vanessa,

Antheaume Cyril,

Nicolas Marc,

Mioskowski Charles,

Baati Rachid

Publication year - 2009

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.200900960

Subject(s) - chemistry , yield (engineering) , molten salt , selectivity , salt (chemistry) , organic chemistry , medicinal chemistry , combinatorial chemistry , inorganic chemistry , catalysis , materials science , metallurgy

An expeditious, three‐step synthesis of rhein ( 2 ) was optimized starting from bis( N , N ‐diethyl)‐5‐methoxybenzene‐1,3‐dicarboxamide. The key final step, involving deprotection/cyclization of ortho ‐benzoylbenzoic acid 9 in acidic chloroaluminate molten salts, yielded the desired natural product with high selectivity and good overall yield by precluding the competitive Hayashi rearrangement.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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