TY - JOUR
T1 - Catalytic, Enantioselective Syn-Oxyamination of Alkenes
AU - Mumford, Emily M.
AU - Hemric, Brett N.
AU - Denmark, Scott E.
N1 - Funding Information:
The authors are grateful to the National Science Foundation (NSF CHE 1664376 and CHE 2102232) for generous financial support. The authors are indebted to Dr. Zhonglin Tao and Dr. Bradley B. Gilbert for synthesis of several substrates. The authors also thank the UIUC SCS support facilities (microanalysis, mass spectrometry, and NMR) for their assistance.
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/8/25
Y1 - 2021/8/25
N2 - The chemo-, regio-, diastereo-, and enantioselective 1,2-oxyamination of alkenes using selenium(II/IV) catalysis with a chiral diselenide catalyst is reported. This method uses N-tosylamides to generate oxazoline products that are useful both as protected 1,2-amino alcohol motifs and as chiral ligands. The reaction proceeds in good yields with excellent enantio- and diastereoselectivity for a variety of alkenes and pendant functional groups such as sulfonamides, alkyl halides, and glycol-protected ketones. Furthermore, the rapid generation of oxazoline products is demonstrated in the expeditious assembly of chiral PHOX ligands as well as diversely protected amino alcohols.
AB - The chemo-, regio-, diastereo-, and enantioselective 1,2-oxyamination of alkenes using selenium(II/IV) catalysis with a chiral diselenide catalyst is reported. This method uses N-tosylamides to generate oxazoline products that are useful both as protected 1,2-amino alcohol motifs and as chiral ligands. The reaction proceeds in good yields with excellent enantio- and diastereoselectivity for a variety of alkenes and pendant functional groups such as sulfonamides, alkyl halides, and glycol-protected ketones. Furthermore, the rapid generation of oxazoline products is demonstrated in the expeditious assembly of chiral PHOX ligands as well as diversely protected amino alcohols.
UR - http://www.scopus.com/inward/record.url?scp=85114034292&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85114034292&partnerID=8YFLogxK
U2 - 10.1021/jacs.1c06750
DO - 10.1021/jacs.1c06750
M3 - Article
C2 - 34375090
AN - SCOPUS:85114034292
VL - 143
SP - 13408
EP - 13417
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 33
ER -