一种用于二氢菲稠合螺环氧化吲哚的非对映选择性策略 [1,2]-磷杂-Brook重排。
A diastereoselective strategy for dihydrophenanthrene-fused spirooxindoles [1,2]-phospha-Brook rearrangement.
作者信息
Ali Amjad, Harit Harish K, Behera Chandana, Singh Ravi P
机构信息
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
出版信息
Chem Commun (Camb). 2024 Aug 15;60(67):8904-8907. doi: 10.1039/d4cc02215g.
A highly diastereoselective, one-pot strategy for spirooxindoles bearing dihydrophenanthrenes from readily available isatins and -quinone methides (-QMs) has been disclosed. Here, a sequential umpolung process [1,2]-phospha-Brook rearrangement followed by Lewis acid-mediated intramolecular cyclization was employed to furnish the desired spiro product. This protocol provides access to potential medicinally relevant varieties of spirooxindolyl dihydrophenanthrenes in good to excellent yields and diastereoselectivity (>20 : 1).
已公开了一种从易得的异吲哚酮和醌甲基化物（-QMs）合成含二氢菲的螺氧化吲哚的高度非对映选择性一锅法策略。在此，采用了顺序极性翻转过程——[1,2]-磷杂-Brook重排，随后是路易斯酸介导的分子内环化，以提供所需的螺环产物。该方法能够以良好至优异的产率和非对映选择性（>20:1）获得潜在的具有医学相关性的螺氧化吲哚基二氢菲品种。
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