Asymmetric Autocatalysis Enables an Improved Synthesis of Efavirenz

被引:77
作者
Chinkov, Nicka [1 ]
Warm, Aleksander [1 ,2 ]
Carreira, Erick M. [1 ]
机构
[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
[2] Lonza AG, CH-3930 Visp, Switzerland
关键词
asymmetric catalysis; autocatalysis; efavirenz; tertiary alkynols; zinc acetylides; HIGHLY ENANTIOSELECTIVE ADDITION; PHENYLACETYLENE ADDITION; CARBONYL-COMPOUNDS; TERMINAL ALKYNES; ALKYNYLATION; ALDEHYDES; KETONES; AUTOINDUCTION; AMPLIFICATION; ALCOHOLS;
D O I
10.1002/anie.201006689
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Priming the pump: An asymmetric autocatalytic zinc acetylide addition employs catalytic amounts of the enantiomerically pure product as part of a chiral cocktail. This new strategy enables an improved synthesis of a key precursor to efavirenz (see scheme). © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2957 / 2961
页数:5
相关论文
共 68 条