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CH Functionalization/CO Bond Cleavage of Benzyl Silyl Ethers with Ynamides for the Chemoselective Synthesis of Skeletally Diverse Compounds
Author(s) -
Chen Ling,
Yu Lian,
Deng Yuan,
Zheng ZhanJiang,
Xu Zheng,
Cao Jian,
Xu LiWen
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500936
Subject(s) - silylation , chemistry , carbocation , annulation , cycloaddition , surface modification , lewis acids and bases , cleavage (geology) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
Described here is a practical carbocation‐initiated formal [3+2] or [4+2] cycloaddition reaction for the diversity‐oriented syntheses of 1‐amidoindenes and 2‐amido‐4 H ‐chromenes. The Lewis acid‐promoted annulation of ynamides and benzyl silyl ethers efficiently constructs 1‐amidoindenes via CH functionalization of benzyl silyl ethers. By utilization of o ‐methoxybenzyl silyl ethers, 2‐amido‐4 H ‐chromenes are also constructed via CO bond cleavage of benzyl silyl ethers.