模块化设计有机催化剂催化的六氢-6H-苯并[c]色烯-6-酮衍生物的非对映发散合成
Diastereodivergent Synthesis of Hexahydro-6H-benzo[c]chromen-6-one Derivatives Catalyzed by Modularly Designed Organocatalysts.
作者信息
Jakkampudi Satish, Parella Ramarao, Arman Hadi D, Zhao John C-G
机构信息
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas, 78249-0698, USA.
出版信息
Chemistry. 2019 Jun 4;25(31):7515-7520. doi: 10.1002/chem.201806447. Epub 2019 May 9.
Abstract
The diastereodivergent synthesis of hexahydro-6H-benzo[c]chromen-6-one derivatives with good to high diastereoselectivities (up to 98:2 d.r.) and enantioselectivities (up to >99 % ee) has been achieved by using a domino Michael/Michael/hemiacetalization reaction between trans-2-hydroxy-β-nitrostyrenes and trans-7-oxo-5-heptenals followed by oxidation. With use of appropriate modularly designed organocatalysts (MDOs) that are self-assembled in situ from amino acid derivatives and cinchona alkaloid derivatives, two different diastereomers of the desired hexahydro-6H-benzo[c]chromen-6-ones are obtained from the same substrates.
摘要
通过反式-2-羟基-β-硝基苯乙烯与反式-7-氧代-5-庚烯醛之间的多米诺迈克尔/迈克尔/半缩醛化反应，随后进行氧化，已实现了具有良好至高非对映选择性（高达98:2的非对映体比例）和对映选择性（高达>99% ee）的六氢-6H-苯并[c]色烯-6-酮衍生物的非对映发散合成。通过使用由氨基酸衍生物和金鸡纳生物碱衍生物原位自组装的适当模块化设计有机催化剂（MDO），从相同底物中获得了所需六氢-6H-苯并[c]色烯-6-酮的两种不同非对映体。
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