Copper-Catalyzed Asymmetric Allylic Alkylation of Halocrotonates: Efficient Synthesis of Versatile Chiral Multifunctional Building Blocks

被引：39
作者：
den Hartog, Tim [1 ]
Macia, Beatriz [1 ]
Minnaard, Adriaan J. [1 ]
Feringa, Ben L. [1 ]
机构：
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 06期
关键词：
asymmetric catalysis; carbon-carbon bond formation; copper catalysis; Grignard reagents; multifunctional building blocks; ENANTIOSELECTIVE CONJUGATE ADDITION; GRIGNARD-REAGENTS; STEREOSELECTIVE-SYNTHESIS; CLAISEN REARRANGEMENT; CROSS-METATHESIS; CARBOXYLIC-ACIDS; ABSOLUTE-CONFIGURATION; ESTERS; HYDROGENATION; ALCOHOLS;
D O I：
10.1002/adsc.201000109
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The highly enantioselective synthesis of alpha-methyl-substituted esters is reported in up to 90% yield and up to 99% ee using copper-TaniaPhos as chiral catalyst. The transformation proved scalable to at least 6.6 mmol (1.7 g scale). The products of this transformation have been further elaborated to multifunctional building blocks with a single (branched esters and acids) or multiple stereogenic centers (vicinal dimethyl esters, as well as, hydroxy- or iodo-substituted lactones).
引用
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页码：999 / 1013
页数：15
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