Cyclisation of Aminyl Radicals Derived from Amino Acids

α-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu3SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions onto suitably placed N-alkenyl or α-alkenyl chains on the amino acids with reasonable diastereoselectivity. The α-ester of the amino acid imparts el...

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Bibliographic Details
Published inTetrahedron letters Vol. 38; no. 35; pp. 6301 - 6304
Main Authors Bowman, W.Russell, Broadhurst, Michael J, Coghlan, Daniel R, Lewis, Kirk A
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.09.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HYDRAZONES
AMIDYL RADICALS
IMINES
KINETICS
RATE CONSTANTS
SULFENAMIDE PRECURSORS
CYCLIZATION
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Summary:α-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu3SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions onto suitably placed N-alkenyl or α-alkenyl chains on the amino acids with reasonable diastereoselectivity. The α-ester of the amino acid imparts electrophilic behaviour to the aminyl radicals and facilitates cyclisation onto alkenes. © 1997 Elsevier Science Ltd.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01413-5