Stereoselective Organocatalytic Synthesis of  γ,γ‐ Disubstituted Butenolides | Zendy

Sharma Vivek | Zendy; Bhardwaj Vimal K. | Zendy; Chimni Swapandeep S. | Zendy

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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.

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