Highly flexible synthesis of chiral azacycles via iridium-catalyzed hydrogenation.
A range of saturated chiral azacycles has been prepared in high yield and with high selectivity from simple starting materials. A modular approach with ring-closing metathesis as a key step was used to produce a number of five-, six-, and seven-membered cyclic alkenes. Asymmetric hydrogenation catalyzed by N,P-ligated iridium complexes gave saturated azacycles in high optical purity. This methodology was demonstrated in the synthesis of a pharmaceutical precursor.
Verendel
J Johan
JJ
Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, S-75123 Uppsala, Sweden.
Zhou
Taigang
T
Li
Jia-Qi
JQ
Paptchikhine
Alexander
A
Lebedev
Oleg
O
Andersson
Pher G
PG
D000475:Alkenes / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D014105:Tosyl Compounds / Q000737:chemistry
D000475:Alkenes; D001372:Aza Compounds; D011725:Pyridines; D014105:Tosyl Compounds; D007495:Iridium; C023666:pyridine