Chiral Propargylic Cations as Intermediates in S1-Type Reactions: Substitution Pattern, Nuclear Magnetic Resonance Studies, and Origin of the Diastereoselectivity.

Nine propargylic acetates, bearing a stereogenic center (-CHXR) adjacent to the electrophilic carbon atom, were prepared and subjected to S1-type substitution reactions with various silyl nucleophiles employing bismuth trifluoromethanesulfonate [Bi(OTf)] as the Lewis acid. The diastereoselectivity o...

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Bibliographic Details

Published in:	Journal of the American Chemical Society Vol. 136; no. 7; pp. 2851 - 2858
Main Authors:	Nitsch, Dominik, Huber, Stefan M., Pöthig, Alexander, Narayanan, Arjun, Olah, George A., Surya Prakash, G. K., Bach, Thorsten
Format:	Article
Published:	American Chemical Society 2/19/2014
Subjects:	Density functionals Scission (Chemistry) Chemical reactions Native element minerals Acid-base chemistry Magnetic resonance Cations
Online Access:	View this record in EBSCOhost