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Construction of 3,4‐Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters: Organocatalytic Asymmetric Michael Addition of 2‐Oxochroman‐3‐carboxylate Esters to trans ‐ β ‐Nitroolefins
Author(s) -
Jin Hui,
Cho Soo Min,
Hwang GeumSook,
Ryu Do Hyun
Publication year - 2017
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.201600825
Subject(s) - stereocenter , chemistry , carboxylate , yield (engineering) , adduct , michael reaction , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , materials science , metallurgy
An asymmetric Michael addition of 2‐oxochroman‐3‐carboxylate esters to trans‐β‐ nitroolefins is described. This strategy can give direct access to dihydrocoumarin derivatives bearing adjacent quaternary and tertiary stereocenters with up to >99% yield, >20:1 dr , and >99% ee . The adduct was further transformed to a spiro‐dihydrocoumarin compound in three steps with good yield.