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Organocatalytic Enantioselective Michael‐Aldol[3+2] Annulation for the Synthesis of Nitro‐Methanobenzo[7] annulenes
Author(s) -
Zhang Yang,
Liu JinYu,
Zhang XiaoHai
Publication year - 2021
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.202100974
Subject(s) - enantioselective synthesis , annulation , chemistry , annulene , bifunctional , aldol reaction , nitro , thiourea , michael reaction , organocatalysis , total synthesis , organic chemistry , catalysis , stereochemistry , combinatorial chemistry , alkyl
We report an enantioselective Michael‐Aldol [3+2] annulation between 2‐alkyl‐3‐hydroxynaphthalene‐1,4‐diones and nitroalkenes using a bifunctional thiourea catalyst, and a series of nitro‐methanobenzo[7]annulenes with potential biological activities were synthesized in good yields with excellent enantio‐ and diastereoselectivities. A gram‐scale synthesis and further transformation of the product demonstrated the synthetic value of this reaction.