Organocatalyzed Enantioselective Synthesis of Quaternary Carbon‐Containing Isoindolin‐1‐ones
Organocatalyzed Enantioselective Synthesis of Quaternary Carbon‐Containing Isoindolin‐1‐ones
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DOI：
10.1002/ejoc.201100163
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发表时间：
2011-06
影响因子：
2.8
通讯作者：
Xiaolei Yu;Y. Wang;Guiping Wu;Hai-bin Song;Zhenghong Zhou;Chuchi Tang
中科院分区：
文献类型：
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作者：
Xiaolei Yu;Y. Wang;Guiping Wu;Hai-bin Song;Zhenghong Zhou;Chuchi Tang
3，3 ′-三苯基硅基取代的（S）-BINOL基（1，1 ′-联-2-萘酚）磷酸已被证明是吲哚与3-取代的3-羟基异吲哚啉-1-酮的不对称Friedel-Crafts烷基化反应的有效有机催化剂，得到相应的含季碳的3，3-二取代的异吲哚啉-1-酮，产率高（高达99%），对映选择性高（高达95%ee）。经一次重结晶后，产品的光学纯度进一步提高。该方法为催化不对称合成3，3-二取代异吲哚啉-1-酮提供了一种简便的方法，具有较高的产率和对映选择性。
3,3′-Triphenylsilyl-substituted (S)-BINOL-based (1,1′-bi-2-naphthol) phosphoric acid has proven to be an effective organocatalyst for the asymmetric Friedel–Crafts alkylation of indoles with 3-substituted 3-hydroxyisoindolin-1-ones, affording the corresponding quaternary carbon-containing 3,3-disubstituted isoindolin-1-ones in good yields (up to 99 %) with good to excellent enantioselectivities (up to 95 % ee). The optical purity of the product was further improved after a single recrystallization. This protocol provides a convenient method for the catalytic asymmetric synthesis of valuable 3,3-disubstituted isoindolin-1-ones in high yields and enantioselectivities.