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Enantioselective Synthesis of Functionalized Diazaspirocycles from 4‐Benzylideneisoxazol‐5(4 H )‐one Derivatives and Isocyanoacetate Esters
Author(s) -
MartínezPardo Pablo,
Laviós Adrián,
SanzMarco Amparo,
Vila Carlos,
Pedro José R.,
Blay Gonzalo
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.202000611
Subject(s) - chemistry , enantioselective synthesis , stereocenter , diastereomer , cinchona , enantiomer , cycloaddition , cyclohexenone , bifunctional , organic chemistry , organocatalysis , squaramide , enantiomeric excess , lewis acids and bases , stereochemistry , catalysis , combinatorial chemistry
Abstract Enantioenriched spirocyclic compounds bearing three contiguous stereocenters and high functionalization were obtained through a formal [3+2] cycloaddition reaction catalyzed by a cooperative system. The spiro compounds were synthesized from 4‐arylideneisoxazol‐5‐ones and isocyanoacetate esters using a bifunctional squaramide/Brønsted base organocatalyst derived from a Cinchona alkaloid and silver oxide as Lewis acid. This method afforded two out of the four possible diastereomers with good yields and high enantiomeric excess for both diastereomers.