TY - JOUR
T1 - Reactions of 5-Aminoisoxazoles with α-Diazocarbonyl Compounds
T2 - Wolff Rearrangement vs N-H Insertion
AU - Ge, Yun
AU - Sun, Wangbin
AU - Chen, Yang
AU - Huang, Yulin
AU - Liu, Zhuang
AU - Jiang, Yaojia
AU - Loh, Teck Peng
N1 - Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/3/1
Y1 - 2019/3/1
N2 - A highly chemoselective reaction between 5-aminoisoxazoles and α-diazocarbonyl compounds has been described. Both Wolff rearrangement and N-H insertion products can be obtained selectively by the judicious choice of reaction conditions. In the case of the Wolff rearrangement reactions, the N-isoxazole amides are accessed as the sole products under thermal conditions. On the other hand, α-amino acid derivatives of N-isoxazolescan be obtained through N-H insertion reactions in the presence of catalytic Rh 2 (Oct) 4 . Both reactions proceed under mild reaction conditions and feature a broad substrate scope.
AB - A highly chemoselective reaction between 5-aminoisoxazoles and α-diazocarbonyl compounds has been described. Both Wolff rearrangement and N-H insertion products can be obtained selectively by the judicious choice of reaction conditions. In the case of the Wolff rearrangement reactions, the N-isoxazole amides are accessed as the sole products under thermal conditions. On the other hand, α-amino acid derivatives of N-isoxazolescan be obtained through N-H insertion reactions in the presence of catalytic Rh 2 (Oct) 4 . Both reactions proceed under mild reaction conditions and feature a broad substrate scope.
UR - http://www.scopus.com/inward/record.url?scp=85061894800&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85061894800&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b02986
DO - 10.1021/acs.joc.8b02986
M3 - Article
C2 - 30702883
AN - SCOPUS:85061894800
SN - 0022-3263
VL - 84
SP - 2676
EP - 2688
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -