ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Asymmetric methylation and phenylation of the chiral pyridinium salt 7, as well as methylation of chiral pyridinium salt 18, with Grignard reagents occurred in good yield and with good-to-excellent diastereoselectivities (Schemes 2 and 3, resp.). These results are best explained by assuming chelate control to govern the asymmetric alkylation/arylation process. The minimum-energy conformations of the out-of-plane twisted pyridinium salts 7 and 18, as determined by the ‘Molecular Simulations Cerius-Dreiding II’ program, are in good agreement with the postulated asymmetric chelate-control mechanism.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19950780106