Abstract
In Diels-Alder reactions of 1-acyloxydienes, the 1- O-methylmandeloxy group has the distinct advantage of serving dual functions. Not only is it an effective chiral auxiliary for Diels-Alder stereocontrol, but also it provides rather reliable determination of the absolute stereochemistry of the Diels-Alder adduct, via the Dale-Mosher NMR model, subject only to the ability to resolve the proper NMR resonances. Study of the Diels-Alder reactions of such chiral 1-acyloxydienes has led us to a transition structure model which uniquely explains the origin of the observed stereoselectivities and is supported by experimental evidence, including X-ray structures showing the conformations of three Diels-Alder adducts. The model may also have wider applicability in conformational analysis and control of selectivity in other reactions.
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.