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Stereoselective Organocatalytic Synthesis of γ,γ‐ Disubstituted Butenolides
Author(s) -
Sharma Vivek,
Bhardwaj Vimal K.,
Chimni Swapandeep S.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801217
Subject(s) - stereocenter , enantiopure drug , enantioselective synthesis , butenolide , cinchona , stereoselectivity , chemistry , stereochemistry , yield (engineering) , organocatalysis , combinatorial chemistry , catalysis , organic chemistry , materials science , metallurgy
A direct highly diastereo‐ and enantioselective asymmetric doubly vinylogous 1,6‐Michael addition reaction of 3‐methyl‐4‐nitro‐5‐alkenyl isoxazoles with γ ‐substituted deconjugated butenolides has been successfully developed with the help of Cinchona derived squaramides. This novel strategy has been utilized to synthesize a range of enantiopure γ,γ ‐disubstituted butenolide molecules bearing remote contiguous quaternary and tertiary stereocenters in yield up to 76% with ee up to 98% and dr up to ≥20:1.