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Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings
Author(s) -
Yokoe Hiromasa,
Mizumura Yuka,
Sugiyama Kana,
Yan Kejia,
Hashizume Yuna,
Endo Yuto,
Yoshida Sae,
Kiriyama Akiko,
Tsubuki Masayoshi,
Kanoh Naoki
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202001179
Subject(s) - intramolecular force , surface modification , domino , natural product , combinatorial chemistry , chemistry , benzene , stereochemistry , suzuki reaction , organic chemistry , catalysis , palladium
Here we describe the diastereoselective synthesis of (5 r ,8 r )‐1,9‐diazadispiro[4.2.4 8 .2 5 ]tetradecatrienes via domino double spirocyclization of N ‐arylamide derivatives. This reaction can serve as a fast way to synthesize diazadispirocycles, which are found in the core structures of bioactive natural products. Product diversification via Suzuki–Miyaura cross coupling and application to the synthesis of 1‐oxa‐9‐azadispiro[4.2.4 8 .2 5 ]tetradecatrienes were also conducted.