对映选择性地将 PhSCFSiMe 添加到手性 --丁烷亚磺酰基酮亚胺中，该酮亚胺衍生自色胺：手性 -二氟亚甲基化螺吡咯烷和螺哌啶基氧化吲哚的合成。
Diastereoselective Addition of PhSCFSiMe to Chiral --Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched -Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles.
机构信息
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok10400, Thailand.
Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla90110, Thailand.
出版信息
J Org Chem. 2022 Dec 2;87(23):15963-15985. doi: 10.1021/acs.joc.2c02098. Epub 2022 Nov 11.
A convenient and efficient synthetic strategy to prepare enantioenriched -difluoromethylenated spiro-pyrrolidinyl and spiro-piperidinyl oxindoles is described. Fluoride-mediated diastereoselective nucleophilic addition of PhSCFSiMe to chiral --butanesulfinyl ketimines derived from isatins was a key step and provided diastereomeric adducts, which were readily separable. Removal of the chiral sulfinyl group followed by structural manipulation afforded chiral -difluoromethylenated spiro-pyrrolidinyl and spiro-piperidinyl oxindoles.
描述了一种方便高效的合成对映富集的 -二氟亚甲基螺吡咯啶基和螺哌啶基氧化吲哚的策略。氟化物介导的对映选择性亲核加成PhSCFSiMe 到来自色满酮的手性 --丁烷亚砜基酮亚胺是关键步骤，提供了非对映异构体加成物，它们很容易分离。手性亚砜基的去除，然后进行结构修饰，得到了手性 -二氟亚甲基螺吡咯啶基和螺哌啶基氧化吲哚。
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