TY - JOUR
T1 - Enantiopure trans -4,5-disubstituted 2-imidazolidinones via copper(I)-catalyzed ring opening of 1,1′-DiBoc-2,2′-biaziridine with grignard reagents
AU - Kennedy, Matthew D.
AU - Bailey, Stephen J.
AU - Wales, Steven M.
AU - Keller, Paul A.
PY - 2015/6/5
Y1 - 2015/6/5
N2 - The copper-catalyzed ring opening of chiral-pool-derived 1,1′-diBoc-2,2′-biaziridine with Grignard reagents affords enantiopure 2-imidazolidinones in a desymmetrizing, cascade process involving the Boc protecting group. This divergent strategy provides reaction-ready, N-differentiated products and allows two C-C bond constructions concurrent to imidazolidinone formation. A variety of alkyl, cyclic, and aryl Grignard reagents are tolerated in reasonable to good yields.
AB - The copper-catalyzed ring opening of chiral-pool-derived 1,1′-diBoc-2,2′-biaziridine with Grignard reagents affords enantiopure 2-imidazolidinones in a desymmetrizing, cascade process involving the Boc protecting group. This divergent strategy provides reaction-ready, N-differentiated products and allows two C-C bond constructions concurrent to imidazolidinone formation. A variety of alkyl, cyclic, and aryl Grignard reagents are tolerated in reasonable to good yields.
UR - http://www.scopus.com/inward/record.url?scp=84930684856&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b00832
DO - 10.1021/acs.joc.5b00832
M3 - Article (Academic Journal)
C2 - 25938909
AN - SCOPUS:84930684856
SN - 0022-3263
VL - 80
SP - 5992
EP - 5998
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 11
ER -