期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 12, 期 4, 页码 574-580出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob42100g
关键词
-
资金
- Department of Science and Technology (DST), New Delhi [DST/SR/S1/OC-65/2008]
- Council of Scientific and Industrial Research (CSIR), New Delhi
Asymmetric synthesis of drug-like functionalized spiro[chroman-3,3'-indolinl-2'-ones 5 containing three contiguous stereocenters with high diastereo- and enantioselectivities was achieved using the reflexive-Michael (r-M) reaction of unmodified hydroxyenals 1 with various (E)-3-alkylideneindolin-2-ones 2 in the presence of (R)-DPPOTMS/AcOH (R)-3/4b as a catalyst at room temperature. Chiral spiro[chroman-3,3'-indolin]-2'-ones 5 were transformed into the functionalized spiranes 7, 9, and 10 in good yields with high selectivity through Wittig. TCRA, acetal protection and reduction reactions, respectively. Supporting evidence for the reaction pathway through the formation of the important catalytic species of aminals was observed through NMR and ESI-HRMS analysis of an ongoing reaction between 1 and (R)-3 in CDCl3 and also shown by the structural requirement in hydroxyenals 1 to generate the aminals with (R)-3 through controlled experiments.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据