A NEW PINANE-TYPE TRIDENTATE MODIFIER FOR ASYMMETRIC REDUCTION OF KETONES WITH LITHIUM ALUMINUM-HYDRIDE

Authors
CHERNG YJ FANG JM LU TJ
Citation
Yj. Cherng et al., A NEW PINANE-TYPE TRIDENTATE MODIFIER FOR ASYMMETRIC REDUCTION OF KETONES WITH LITHIUM ALUMINUM-HYDRIDE, Tetrahedron : asymmetry, 6(1), 1995, pp. 89-92
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
1
Year of publication
1995
Pages
89 - 92
Database
ISI
SICI code
0957-4166(1995)6:1<89:ANPTMF>2.0.ZU;2-E
Abstract
The reduction of aryl and alkenyl methyl ketones using lithium aluminu m hydride modified with ,2S,3S,5R)-(+)-10-anilino-3-ethoxy-2-hydroxypi nane (3), afforded chiral secondary alcohols in 83-96% yields and 53-9 7% optical yields. The modifier 3 was prepared from (1R)-(-)-myrtenol and was readily recovered (>96%) after reduction. The reduction of ace tophenone in the presence of lithium iodide gave the alcohol product w ith higher optical yield.