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Carbonyl‐Oxygen‐Assisted KOMe‐Mediated Formal Hydration of 4‐Alkynones: Complete Regioselectivity in the One‐Pot Synthesis of 1,4‐Diketones under Mild Conditions
Author(s) -
Bai XueTing,
Zhang QianQian,
Zhang Shuai,
Chen DanYun,
Fu JiYa,
Zhu JunYan,
Wang YanBo,
Tang YanTing
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800024
Subject(s) - chemistry , regioselectivity , one pot synthesis , organic chemistry , combinatorial chemistry , catalysis
An effective carbonyl‐oxygen‐assisted transition‐metal‐free approach was developed for the one‐pot synthesis of 1,4‐diketones through the formal hydration of 4‐alkynones with complete regioselectivity under mild conditions. The reaction tolerates a wide range of functional groups, and the corresponding functionalized 1,4‐diketones were obtained in moderate to excellent yields (up to 94 %). Importantly, the complete regioselectivity was attributed to the fact that 2,3‐dihydrofuran intermediates were obtained as single products through the 5‐ exo ‐ dig cyclization of 4‐alkynones; this was supported by control and isotope‐labeling experiments.