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Development of Novel Chloramphenicol Scaffold‐Based Chiral Hydroxyl Oxazoline Ligands and Their Application to the Asymmetric Alkynylation of Isatins
Author(s) -
Chen Lei,
Huang Guanxin,
Liu Minjie,
Huang Zedu,
Chen FenEr
Publication year - 2018
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.201800581
Subject(s) - chemistry , alkynylation , oxazoline , enantioselective synthesis , catalysis , combinatorial chemistry , substrate (aquarium) , functional group , organic chemistry , oceanography , polymer , geology
The synthesis of new chloramphenicol base‐derived chiral hydroxyl oxazoline ligands, and their use in the first Zn(OTf) 2 ‐catalyzed enantioselective alkynylation of isatins are described. This transformation features mild reaction conditions, a remarkably broad substrate scope, and excellent functional group tolerance, affording the corresponding tertiary propargylic alcohols in high yields and with high enantioselectivities. The application of chiral hydroxyl oxazolines as ligands in Zn(II)‐catalyzed asymmetric alkynylation reactions is unprecedented.