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Enantio- and Stereoselective Construction of Atisane Scaffold via Organocatalytic Intramolecular Michael Reaction and Diels–Alder Reaction

Author:
Sekita, Hiroko, Adachi, Kyohei, Kobayashi, Ippei, Sato, Yusuke, Nakada, Masahisa
Source:
Organic letters 2017 v.19 no.9 pp. 2390-2393
ISSN:
1523-7052
Subject:
benzoic acid, catalytic activity, chemical reactions, chemical structure, stereoselectivity, thiourea
Abstract:
An enantio- and stereoselective construction of the atisane scaffold via organocatalytic intramolecular Michael reaction and Diels–Alder reaction is described. The organocatalytic intramolecular Michael reaction has been found to stereoselectively generate a trans-stereodiad comprising an all-carbon quaternary and a tertiary stereogenic centers. Use of the chiral secondary amine bearing thiourea with benzoic acid as additive is the key to obtaining the desired product with excellent ee in synthetically acceptable yield. The prepared chiral building block has been successfully converted to the compound including the atisane scaffold via the highly stereoselective intramolecular Diels–Alder reaction.
Agid:
5794062