TY - JOUR
T1 - Pd-Catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates
AU - Gee, Yi Sing
AU - Rivinoja, Daniel J.
AU - Wales, Steven M.
AU - Gardiner, Michael G.
AU - Ryan, John H.
AU - Hyland, Christopher J.T.
PY - 2017/12/15
Y1 - 2017/12/15
N2 - A trans-diastereoselective Pd-catalyzed dearomative [3 + 2] cycloaddition between vinylcyclopropane dicarboxylates and 3-nitroindoles has been developed. The reaction provides densely functionalized cyclopenta[b]indolines with versatile vinyl and nitro-groups. The addition of a halide additive was found to be critical for the diastereoselectivity of the reaction, which is proposed to be a result of a rapid π-σ-π interconversion between the intermediates allowing for Curtin-Hammett control. A switch in diastereoselectivity to afford products with the vinyl and nitro groups cis to each other is observed with a 4-substituted 3-nitroindole.
AB - A trans-diastereoselective Pd-catalyzed dearomative [3 + 2] cycloaddition between vinylcyclopropane dicarboxylates and 3-nitroindoles has been developed. The reaction provides densely functionalized cyclopenta[b]indolines with versatile vinyl and nitro-groups. The addition of a halide additive was found to be critical for the diastereoselectivity of the reaction, which is proposed to be a result of a rapid π-σ-π interconversion between the intermediates allowing for Curtin-Hammett control. A switch in diastereoselectivity to afford products with the vinyl and nitro groups cis to each other is observed with a 4-substituted 3-nitroindole.
UR - http://www.scopus.com/inward/record.url?scp=85038436609&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b02624
DO - 10.1021/acs.joc.7b02624
M3 - Article (Academic Journal)
C2 - 29129063
AN - SCOPUS:85038436609
SN - 0022-3263
VL - 82
SP - 13517
EP - 13529
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -