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Oxidative α‐Acetoxylation of a β‐Oxime Ester with (Diacetoxyiodo)benzene Catalyzed by Sc III Salts: An Approach to the Docetaxel Side Chain
Author(s) -
Miyamoto Kazunori,
Hoque Md. Mahbubul,
Senoh Yuhki,
Ali Mohammad Idrish,
Nemoto Hisao,
Mandai Tadakatsu
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.201800292
Subject(s) - chemistry , hypervalent molecule , catalysis , hydroxylation , oxidative phosphorylation , hydrolysis , medicinal chemistry , oxime , reagent , iodine , organic chemistry , oxidative addition , enzyme , biochemistry
Hypervalent iodine(III) compounds have emerged as reagents of choice for α‐oxidation of various ketones under mild reaction conditions. We report herein a simple method for α‐hydroxylation of a β‐oxime ester, which involves an oxidative α‐acetoxylation using PhI(OAc) 2 with a catalytic amount of Sc(OTf) 3 or Sc 2 O 3 ‐TMSOTf, followed by careful hydrolysis. The scandium(III) salt serves as an excellent reusable catalyst in this system.