Abstract
Restricted rotation about the Ar-CO bond means that 1-naphthamides bearing chiral 8-substituents may exist as pairs of diastereoisomeric atropisomers. These atropisomers are formed with good to excellent stereoselectivity for the syn-diastereoisomer by the reaction of 8-formyl-1-naphthamides with organolithiums and Grignard reagents. The reduction of 8-acyl-l-naphthamides also proceeds with syn-selectivity. The product alcohols are prone to lactonisation and also to epimerisatiori, and some of the apparent diastereoselectivities may be the result of thermodynamic, rather than kinetic, control.
Original language | English |
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Pages (from-to) | 1379-1385 |
Number of pages | 7 |
Journal | Perkin 1 |
Issue number | 9 |
DOIs | |
Publication status | Published - 18 Apr 2000 |