Premium
Enantioselective Synthesis of Chromanones through Organocatalytic Tandem Reactions
Author(s) -
Lu Mengxue,
Wang Xin,
Xiong Zongli,
Duan Jingxiang,
Ren Wen,
Yao Weijun,
Xia Yi,
Wang Zhen
Publication year - 2020
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.202001031
Subject(s) - chemistry , enantioselective synthesis , stereocenter , lactone , organocatalysis , amine gas treating , catalysis , organic chemistry , tandem , yield (engineering) , stereochemistry , materials science , metallurgy , composite material
An enantioselective approach to lactone‐fused chromanone derivatives from 1‐(2‐hydroxyaryl)‐1,3‐diketones and α,β‐unsaturated aldehydes under mild conditions has been developed, which included organocatalytic stepwise Michael addition/ cycloketalization/hemiacetalization and followed by oxidation reaction. In the presence of chiral amine organocatalyst and an additional salicylic acid, a wide range of 1‐(2‐hydroxyaryl)‐1,3‐diketones and α,β‐unsaturated aldehydes were tolerated, furnishing a spectrum of lactone‐fused tricyclic chromanones bearing three contiguous stereocenters in high yields with good to excellent selectivities (90‐>99% ee, >19:1 d.r.).