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Asymmetric Synthesis of Carboranyl Amino Acids with Potential use in BNCT
Author(s) -
Sjöberg Stefan,
Hawthorne M. Frederick,
Wilmouth Serge,
Lindström Peter
Publication year - 1995
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19950010707
Subject(s) - amino acid , glycine , chemistry , enantiomer , methanol , camphor , stereochemistry , sodium , derivative (finance) , organic chemistry , biochemistry , financial economics , economics
Two α‐amino acids containing the 1,2‐dicarba‐ closo ‐dodecaborane (12) cage, namely, 5‐(1,2‐dicarba‐ closo ‐dodecaboran (12)‐1‐yl)‐2‐aminopentanoic acid (1) and 5‐(2‐methyl‐1,2‐dicarba‐ closo ‐dodecaboran (12)‐1‐yl)‐2‐aminopentanoic acid ( 2 ), were prepared by asymmetric synthesis (e.p. > 98%) by using the chiral glycine equivalent, imidazolidinone 3 , introduced by Seebach, and Oppolzer's camphor‐derived sultam derivative 4 . The dextrorotatory enantiomers (sodium D line in methanol) of the amino acids 1 and 2 were both shown to have ( S ) configuration.