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Copper‐Catalyzed Enantioselective Synthesis of Oxazolines from Aminotriols via Asymmetric Desymmetrization
Author(s) -
Yamamoto Kosuke,
Tsuda Yutaro,
Kuriyama Masami,
Demizu Yosuke,
Onomura Osamu
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901742
Subject(s) - desymmetrization , oxazoline , enantioselective synthesis , kinetic resolution , chemistry , hydroxymethyl , catalysis , amine gas treating , combinatorial chemistry , organic chemistry , stereochemistry
A copper‐catalyzed enantioselective transformation of tris(hydroxymethyl)aminomethane‐derived aminotriols was developed to provide multisubstituted oxazolines with a tetrasubstituted carbon center. The present transformation consisted of sequential reactions involving mono‐sulfonylation of aminotriols, subsequent intramolecular cyclization to afford prochiral oxazoline diols, and sulfonylative asymmetric desymmetrization of resultant oxazoline diols. In addition, the kinetic resolution process would be involved in the sulfonylative asymmetric desymmetrization step, which would amplify the enantiopurities of the desired products. Various aminotriols were tolerated in the present reaction, affording the desired oxazolines in good to high yields with excellent enantioselectivities. The synthetic utility of the present reaction was demonstrated by the transformation of the optically active oxazoline into a chiral α‐tertiary amine motif.