Journal of Organic Chemistry p. 9313 - 9321 (2019)
Update date:2022-08-10
Topics:
Hashimoto, Yuki
Michimuko, Chiaki
Yamaguchi, Koki
Nakajima, Makoto
Sugiura, Masaharu
With 2-pyridyl benzoates as acylating agents and Zn(OAc)2 as a catalyst, 1,2-diols, 1,3-diols, and catechol were selectively monoacylated. Furthermore, the highly enantioselective desymmetrization of meso-tartrates was achieved for the first time, utilizing 2-pyridyl esters and NiBr2/AgOPiv/Ph-BOX in CH3CN or CuCl2/AgOPiv/Ph-BOX in EtOAc catalyst systems (up to 96% ee). The latter catalyst system was also effective for the kinetic resolution of dibenzyl dl-tartrate.
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