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Diterpenoid Alkaloid Lappaconine Derivative Catalyzed Asymmetric α‐Hydroxylation of β‐Dicarbonyl Compounds with Hydrogen Peroxide
Author(s) -
Li Zhi,
Lian Mingming,
Yang Fan,
Meng Qingwei,
Gao Zhanxian
Publication year - 2014
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.201402019
Subject(s) - chemistry , hydroxylation , hydrogen peroxide , enantioselective synthesis , catalysis , yield (engineering) , alkaloid , derivative (finance) , organic chemistry , terpenoid , stereochemistry , materials science , economics , financial economics , metallurgy , enzyme
A new framework derived from the commercially available diterpenoid alkaloid lappaconitine was evaluated as a Brønsted base catalyst for the enantioselective α‐hydroxylation of β‐dicarbonyl compounds by using 30 % hydrogen peroxide as a green and highly practical source of oxygen. This protocol allows convenient access to the corresponding α‐hydroxy‐β‐oxo esters, α‐hydroxy‐β‐oxo amides and (–)‐kjellmanianone with up to 98 % yield and 92 % ee .