Enantioresolution of 2-methoxy-2-(1-naphtyl)propionic acid using diastereomeric salt formation with chiral phenylethylamine.

Authors :: Miho Kusakari
Yurie Ohta
Hideaki Nakagawa
Hiroshi Katagiri
Tatsuro Kijima
Satoshi Murakami
Shigeru Matsuba
Bunpei Hatano
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Jul2014, Vol. 55 Issue 30, p4114-4116. 3p.
Publication Year :: 2014
Abstract: An enantioresolution of 2-methoxy-2-(1-naphtyl)propionic acid (MαNP acid) using the diastereomeric salt with chiral (R)-phenylethylamine was achieved to give enantiopure (R)-MαNP acid in 29% yield with >99% ee based on rac-MαNP acid. X-ray crystallographic analysis of diastereomeric salt revealed that (R)-MαNP acid was tightly arranged by four independent hydrogen bonds and one CH-π interaction with (R)-phenylethylamine. [ABSTRACT FROM AUTHOR]

Subjects :: *METHOXY group
*PROPIONIC acid
*DIASTEREOISOMERS
*PHENETHYLAMINES
*HYDROGEN bonding
*X-ray crystallography

Language :: English
ISSN :: 00404039
Volume :: 55
Issue :: 30
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 96978020
Full Text :: https://doi.org/10.1016/j.tetlet.2014.05.037

Full Text Access

Tools