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Silver‐Catalyzed Stereoselective [3+2] Cycloadditions of Cyclopropyl‐Indanimines with Carbonyl Compounds
Author(s) -
Hung HsiaoHua,
Liao YiChing,
Liu RaiShung
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300090
Subject(s) - chemistry , stereoselectivity , catalysis , hydrolysis , organic chemistry , synergistic catalysis , transition state , medicinal chemistry
Silver‐catalyzed stereoselective [3+2] cycloadditions between mono‐substituted cyclopropyl‐indanimines and aldehydes are reported. The stereochemical course of the reaction is rationalized with a cyclic transition state. The resulting indanimine cycloadducts are not readily hydrolyzed unless external aldehydes are present with the silver catalyst. Notably, this hydrolysis process leads to a change of stereochemistry for the resulting indanone products.
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