| Autor: |
Shaw SJ; Rigel, Inc., 1180 Veterans Boulevard, South San Francisco, California 94080, USA. sshaw@rigel.com, Goff DA, Boralsky LA, Irving M, Singh R |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2013 Sep 06; Vol. 78 (17), pp. 8892-7. Date of Electronic Publication: 2013 Aug 19. |
| DOI: |
10.1021/jo401352z |
| Abstrakt: |
The first enantioselective route to both enantiomers of cis-1-Boc-3-fluoropiperidin-4-ol, a highly prized building block for medicinal chemistry, is reported. An enantioselective fluorination is employed, taking advantage of the methodology reported by MacMillan, which uses a modified cinchona alkaloid catalyst. In studying the fluorination reaction, we have shown that the catalyst can be replaced by commercially available primary amines, including α-methylbenzylamine, with similar levels of enantioselectivity. The piperidinols are readily crystallized to obtain enantiopure material. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
|
