Premium
N,N′ ‐Dioxide‐Magnesium Ditriflate Complex‐Catalyzed Asymmetric α‐Hydroxylation of β‐Keto Esters and β‐Keto Amides
Author(s) -
Yin Chengkai,
Cao Weidi,
Lin Lili,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2013
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.201300335
Subject(s) - chemistry , hydroxylation , catalysis , magnesium , organic chemistry , enantioselective synthesis , medicinal chemistry , enzyme
The highly catalytic asymmetric α‐hydroxylation of 1‐tetralone‐derived β‐keto esters and β‐keto amides using tert ‐butyl hydroperoxide (TBHP) as the oxidant was realized by a chiral N , N′ ‐dioxide‐magnesium ditriflate [Mg(OTf) 2 ] complex. A series of corresponding chiral α‐hydroxy dicarbonyl compounds was obtained in excellent yields (up to 99%) with excellent enantioselectivities (up to 98% ee ). The products were easily transformed into useful building blocks and the precursor of daunomycin was achieved in an asymmetric catalytic way for the first time.