A Straightforward Organocatalytic Alkylation of 2-Arylacetaldehydes: An Approach towards Bisabolanes

被引：21
作者：
Gualandi, Andrea [1 ]
Canestrari, Pietro [1 ]
Emer, Enrico [1 ]
Cozzi, Pier Giorgio [1 ]
机构：
[1] Alma Mater Studiorum, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 2-3期
关键词：
-alkylation; bisabolanes; curcumene; enamines; Macmillan's catalyst; organocatalysis; ENANTIOSELECTIVE ALPHA-ALKYLATION; HETEROAROMATIC CATIONS; ALDEHYDES; ARYLATION; STEREOCHEMISTRY; (+)-CURCUPHENOL; SESQUITERPENES; AMINOCATALYSIS; INHIBITORS;
D O I：
10.1002/adsc.201300250
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A highly stereoselective organocatalytic -alkylation of 2-arylacetaldehydes with a commercially available carbenium tetrafluoroborate is described. The stereoselective alkylation was carried out in acetonitrile/water, under air in the presence of a commercially available imidazolidinone (MacMillan's catalyst). Key intermediates for the synthesis of bisabolanes were obtained through a simple chemistry. In particular a direct, enantioselective and facile synthesis of (R)-(-)-curcumene is described.
引用
收藏
页码：528 / 536
页数：9
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