四取代手性碳的不对称取代：外消旋 2,2-二取代氮丙啶与 3-取代色酮的催化开环烷基化反应。
Asymmetric substitution at the tetrasubstituted chiral carbon: catalytic ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles.
机构信息
Institute of Transformative Bio-Molecules (WPI-ITbM), and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University , Nagoya, 464-8603, Japan.
出版信息
J Am Chem Soc. 2013 Dec 18;135(50):18706-9. doi: 10.1021/ja411647x. Epub 2013 Dec 10.
PMID:24304152
Abstract
A highly diastereo- and enantioselective ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles is achieved under the catalysis of a chiral 1,2,3-triazolium salt. This reaction represents a hitherto unknown, catalytic stereoselective carbon-carbon bond formation through direct substitution at the tetrasubstituted chiral carbon.
摘要
在手性 1,2,3-三唑翁盐的催化作用下，实现了外消旋 2,2-二取代氮丙啶与 3-取代色酮的高非对映选择性和对映选择性的环开烷基化反应。该反应代表了一种迄今未知的、催化立体选择性的碳-碳键形成反应，通过在四取代手性碳上直接取代来实现。
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