In:
Chemistry – A European Journal, Wiley, Vol. 23, No. 58 ( 2017-10-17), p. 14515-14522
Kurzfassung:
Herein we describe the design and synthesis of a novel family of bifunctional, chiral bicyclo[2.2.1]heptadiene ligands bearing aryl and secondary amido groups, and demonstrate their usefulness in the Rh I ‐catalyzed enantioselective addition reaction of arylboronic acids to N ‐diphenylphosphinyl ( N ‐DPP)‐protected aldimines. Unlike the analogous Rh I ‐catalysts comprising diene ligands substituted with aryl and carboxylic ester groups, or only with aryl groups, the addition reaction proceeded with high stereoselectivity. The protocol tolerated a range of N ‐DPP‐aldimines and arylboronic acids, producing the desired optically active N ‐DPP‐protected amines with yields between 31–99 % and with ee values up to 91–99 %. The synthetic utility of the method was demonstrated by the conversion of N ‐DPP‐protected amine 3 ae into the antifungal agent, bifonazole ( 13 ).
Materialart:
Online-Ressource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.201702509
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2017
ZDB Id:
1478547-X
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