Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249-0698 (USA).
Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7619-23. doi: 10.1002/anie.201404072. Epub 2014 Jun 12.
A highly diastereodivergent synthesis of tetrasubstituted cyclohexanes has been achieved using modularly designed organocatalysts (MDOs) which are self-assembled in situ from amino acids and cinchona alkaloid derivatives. Diastereodivergence is realized through controlling the stereoselectivity of the individual steps of a tandem Michael/Michael reaction. Up to 8 of the 16 possible stereoisomers have been successfully obtained in high stereoselectivities using MDOs for the tandem reaction and an ensuing epimerization. The method was used in the enantioselective synthesis of the natural products (-)-α- and β-lycoranes.
一种使用模块化设计的有机催化剂（MDO）的高非对映选择性合成四取代环己烷的方法已经被实现，这些 MDO 是由氨基酸和金鸡纳生物碱衍生物原位自组装而成的。非对映选择性是通过控制串联迈克尔/迈克尔反应的各个步骤的立体选择性来实现的。使用 MDO 进行串联反应和随后的差向异构化，可以成功地获得多达 16 个可能的立体异构体中的 8 个，具有高的立体选择性。该方法用于天然产物（-）-α-和β-石蒜碱的对映选择性合成。
