남태규
2019-10-15T01:33:35Z
2019-10-15T01:33:35Z
2005-06
SYNTHESIS-STUTTGART, v. 9, Page. 1397-1404
0039-7881
1437-210X
https://www.thieme-connect.com/products/ejournals/html/10.1055/s-2005-865308
https://repository.hanyang.ac.kr/handle/20.500.11754/111093
n-Alkyllithiums were added to alpha,alpha'-disubstituted-1,8-naphthyridines in non-polar solvents Such as Et2O-hexane mixtures. In polar solvents such as THF, alkyllithium acts as a base rather than a nucleophile. Regioselective addition was achieved for substrates capable of five-membered cyclic chelation of the (alkyl)lithium reagent. Substrates with a TBS-protected alcohol as the co-chelating moiety afforded the best combination of yield and regioselectivity. This methodology was Successfully employed in the preparation of two 6-amino-3-pyridinol analogs of pentamethyl-chromanol (PMC), an alpha-tocopherol derivative with its isoprenoid side chain truncated to a methyl group.
This work was supported by the U.S. National Institutes of Health and National Science Foundation through grants to NAP.
en_US
GEORG THIEME VERLAG KG
1,8-naphthyridine
alkyllithium
chelation
solvent effects
alpha-tocopherol
Regioselective addition of n-alkyllithiums to alpha,alpha '-disubstituted-1,8-naphthyridines: Synthesis of 6-amino-3-pyridinol analogs of alpha-tocopherol
Article
9
10.1055/s-2005-865308
1397-1404
SYNTHESIS-STUTTGART
Nam, T.-G.
Wijtmans, M.
Porter, N.A.
Pratt, D.A.
2011209029
E
COLLEGE OF PHARMACY[E]
DEPARTMENT OF PHARMACY
tnam