ENANTIOSELECTIVE SYNTHESIS OF L-CARBORANYLALANINE AND D-CARBORANYLALANINE

Authors
RADEL PA KAHL SB
Citation
Pa. Radel et Sb. Kahl, ENANTIOSELECTIVE SYNTHESIS OF L-CARBORANYLALANINE AND D-CARBORANYLALANINE, Journal of organic chemistry, 61(14), 1996, pp. 4582-4588
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
14
Year of publication
1996
Pages
4582 - 4588
Database
ISI
SICI code
0022-3263(1996)61:14<4582:ESOLAD>2.0.ZU;2-T
Abstract
The enantioselective synthesis of L- and D-carboranylalanine is report ed. Imides 13 and 14 are treated with titanium tetrachloride, DIEA, an d NBS to introduce a bromo functionality in 98:2 ratio at the alpha-ce nter. Azide displacement with TMGA, displacement of the oxazolidinone template with titanium tetrabenzyloxide, and subsequent hydrogenolysis permits L- or D-carboranylalanine to be isolated in high stereoselect ivity and 35-40% yields overall.