Abstract
Effective synthesis of prolinamides of 2-(2-aminocyclohexyl)phenols has been accomplished. The novel prolinamides are demonstrated to catalyze the direct aldol reaction between ketones and aldehydes with high stereoselectivity, thus affording up to 99 : 1 anti/syn diastereomeric and 99 : 1 enantiomeric ratio. Experimental results as well as computational investigations have revealed that the electrophile (e.g. aldehyde) is activated by dual hydrogen bonding with the amide NH and phenolic OH group of the catalyst. A rather large spacing between the H-bond donor groups and its conformational flexibility are remarkable structural features of the most enantioselective catalyst.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.