Premium
N‐Heterocyclic Carbene‐Catalyzed Double Michael Addition: Stereoselective Synthesis of Spirofluorenes and Multisubstituted Indanes
Author(s) -
Xing Fen,
Feng ZeNan,
Wang Ying,
Du GuangFen,
Gu ChengZhi,
Dai Bin,
He Lin
Publication year - 2018
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.201701269
Subject(s) - michael reaction , chemistry , fluorene , carbene , intramolecular force , catalysis , stereoselectivity , organic chemistry , organocatalysis , medicinal chemistry , enantioselective synthesis , polymer
The strong Brønsted basic character of N ‐heterocyclic carbenes (NHCs) has been used to promote the cascade double Michael addition between fluorenes and dienones. Under catalyst loadings of 1–5 mol% of NHC, fluorene reacts with divinyl ketones (DVKs) to afford anti‐spirofluorene compounds in high yields. However, when benzenedi(enones) were employed as Michael acceptors in the presence of 10 mol% of NHC, fluorene undergoes a different inter‐ and intramolecular cascade double Michael addition, providing multi‐substituted indanes in high yields with excellent diastereoselectivity.