Diterpenoid Alkaloid Lappaconine Derivative Catalyzed Asymmetric α‐Hydroxylation of β‐Dicarbonyl Compounds with Hydrogen Peroxide | Zendy

Li Zhi | Zendy; Lian Mingming | Zendy; Yang Fan | Zendy; Meng Qingwei | Zendy; Gao Zhanxian | Zendy

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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 .

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