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Allylic Amination and 1,2‐Diamination with a Modified Diimidoselenium Reagent
Author(s) -
Bruncko Milan,
Khuong TinhAlfredo V.,
Sharpless K. Barry
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199604541
Subject(s) - allylic rearrangement , amination , reagent , tosyl , chemistry , protecting group , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , alkyl
Replacing the tosyl with a nosyl (Ns) group —that is the key to an improved method for both allylic amination of olefins and 1,2‐diamination of 1,3‐dienes. The protecting group recently introduced by Fukuyama et al., the 0 ‐nitrobenzenesulfonyl (nosyl) group, can be employed with diimidoselenium reagents. The resulting nosyl‐amides can be converted into primary and secondary amines in good to excellent yields. An example of this approach is sketched below in reaction (a) (R Me, CH 2 CHCH 2 , CH 2 Ph).