Chiral N-Fmoc-beta-amino alkyl isonitriles derived from amino acids: first synthesis and application in 1-substituted tetrazole synthesis.
A novel class of optically active N-Fmoc-protected amino isonitriles has been described for the first time. Conversion of the carboxyl group of Fmoc-beta-amino acids into an isocyano group has resulted in a new class of N-urethane-protected amino isonitriles. All the isonitriles have been isolated as stable solids, purified, and completely characterized. A synthetic application of the obtained isonitriles has also been demonstrated through the synthesis of 1-substituted tetrazole analogues of amino acids via a 2 + 3 cycloaddition with trimethylsilyl azide.
Sureshbabu
Vommina V
VV
Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560 001, India. hariccb@rediffmail.com
Narendra
N
N
Nagendra
G
G
D000596:Amino Acids / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D000596:Amino Acids; D001386:Azides; D009570:Nitriles; D013777:Tetrazoles; D014297:Trimethylsilyl Compounds