Enantioselective Synthesis of l- and d-Carboranylalanine
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (14) , 4582-4588
- https://doi.org/10.1021/jo952271b
Abstract
The enantioselective synthesis of l- and d-carboranylalanine is reported. Imides 13 and 14 are treated with titanium tetrachloride, DIEA, and NBS to introduce a bromo functionality in 98:2 ratio at the α-center. 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 stereoselectivity and 35−40% yields overall.Keywords
This publication has 10 references indexed in Scilit:
- Hydroboration of alkenylcarboranes: A regiochemical investigationTetrahedron Letters, 1995
- Enantioselective synthesis of S-o-carboranylalanine via methylated bislactim ethers of 2,5-diketopiperazinesTetrahedron, 1995
- A general, convenient way to carborane-containing amino acids for boron neutron capture therapyTetrahedron Letters, 1992
- A simple route to C-monosubstituted carborane derivativesThe Journal of Organic Chemistry, 1992
- Cage opening of parent closo cage carboranes with fluoride ion: formation of 5-fluoro-hexahydro-nido-2,4-dicarbahexaborate(1-) ([5-F-nido-2,4-C2B4H6]-)Inorganic Chemistry, 1991
- Sodium perborate: a mild and convenient reagent for efficiently oxidizing organoboranesThe Journal of Organic Chemistry, 1989
- Synthesis and reactivity of .beta.-lactones derived from L-threonine and related amino acidsThe Journal of Organic Chemistry, 1989
- Reduction d'azides en amines primaires par une methode generale utilisant la reaction de staudingerTetrahedron Letters, 1983
- Hormone‐Receptor Interactions. Synthesis and Conformational Study of cyclo‐L‐CystathionineHelvetica Chimica Acta, 1976
- Oxidation of Active Hydrogen Compounds with 2-ChlorotetramethylguanidineThe Journal of Organic Chemistry, 1966