通过模块化设计的有机催化剂催化的多米诺反应立体选择性合成3-氧杂双环[3.3.1]壬烷-2-酮
Stereoselective Synthesis of 3-Oxabicyclo[3.3.1]nonan-2-ones via a Domino Reaction Catalyzed by Modularly Designed Organocatalysts.
作者信息
Parella Ramarao, Jakkampudi Satish, Arman Hadi, 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, ; phone: (+1)-210-458-5432.
出版信息
Adv Synth Catal. 2019 Jan 11;361(1):208-213. doi: 10.1002/adsc.201800987. Epub 2018 Oct 30.
Abstract
A highly stereoselective method for the synthesis of functionalized 3-oxabicyclo[3.3.1]nonan-2-one derivatives with four contiguous stereogenic centers, including one tetrasubstituted stereogenic center, was realized through an organocatalytic domino Michael-hemiacetalization-Michael reaction of ()-3-aryl-2-nitroprop-2-enols and ()-7-aryl-7-oxohept-5-enals followed by a PCC oxidation. Using the modularly designed organocatalysts (MDOs) self-assembled from alkaloid derivatives and amino acids in the reaction media, the title products were obtained in good yields (up to 84%), excellent diastereoselectivities (> 99:1 dr), and high enantioselectivities (up to 96% ).
摘要
通过（）-3-芳基-2-硝基丙-2-烯醇与（）-7-芳基-7-氧代庚-5-烯醛的有机催化多米诺迈克尔-半缩醛化-迈克尔反应，随后进行PCC氧化，实现了一种高度立体选择性的方法，用于合成具有四个相邻立体ogenic中心（包括一个四取代立体ogenic中心）的官能化3-氧杂双环[3.3.1]壬-2-酮衍生物。使用在反应介质中由生物碱衍生物和氨基酸自组装而成的模块化设计有机催化剂（MDO），以良好的产率（高达84%）、优异的非对映选择性（>99:1 dr）和高对映选择性（高达96%）获得了标题产物。
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