| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346794 | Tetrahedron: Asymmetry | 2011 | 9 Pages |
A novel bifunctional organocatalytic Michael addition of a succinimide-derived pronucleophile to nitro olefins is described. The use of a range of nitro olefins afforded Michael adducts containing contiguous quaternary and tertiary stereogenic centres in high enantioselectivities and moderate diastereoselectivities.
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(S)-Methyl 1-butyl-3-((S)-2-nitro-1-phenylethyl)-2,5-dioxopyrrolidine-3-carboxylateC18H22N2O6[α]D25=+89 (c 0.7, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (S,S)
(R)-Methyl 1-butyl-3-((S)-2-nitro-1-phenylethyl)-2,5-dioxopyrrolidine-3-carboxylateC18H22N2O6[α]D25=-55 (c 0.3, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (R,S)
(S)-Methyl 3-((R)-1-(2-bromophenyl)-2-nitroethyl)-1-butyl-2,5-dioxopyrrolidine-3-carboxylateC18H21BrN2O6[α]D25=+93.3 (c 0.3, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (S,R)
(R)-Methyl 3-((R)-1-(2-bromophenyl)-2-nitroethyl)-1-butyl-2,5-dioxopyrrolidine-3-carboxylateC18H21BrN2O6[α]D25=+68.8 (c 0.5, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (R,R)
(S)-Methyl 1-butyl-3-((R)-1-(2-chlorophenyl)-2-nitroethyl)-2,5-dioxopyrrolidine-3-carboxylateC18H21ClN2O6[α]D24=+49 (c 1, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (S,R)
(R)-Methyl 1-butyl-3-((R)-1-(2-chlorophenyl)-2-nitroethyl)-2,5-dioxopyrrolidine-3-carboxylateC18H21ClN2O6[α]D24=+31 (c 4, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (R,R)
(S)-Methyl 1-butyl-3-((S)-2-nitro-1-p-tolylethyl)-2,5-dioxopyrrolidine-3-carboxylateC19H24N2O6[α]D21=+60 (c 0.5, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (S,S)
(R)-Methyl 1-butyl-3-((S)-2-nitro-1-p-tolylethyl)-2,5-dioxopyrrolidine-3-carboxylateC19H24N2O6[α]D21=-32.4 (c 0.5, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (R,S)
(S)-Methyl 1-butyl-3-((S)-1-(3-methoxyphenyl)-2-nitroethyl)-2,5-dioxopyrrolidine-3-carboxylateC19H24N2O7[α]D24=+48 (c 1, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (S,S)
(R)-Methyl 1-butyl-3-((S)-1-(3-methoxyphenyl)-2-nitroethyl)-2,5-dioxopyrrolidine-3-carboxylateC19H24N2O7[α]D24=-35 (c 0.7, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (R,S)
(S)-Methyl 1-butyl-3-((S)-1-(furan-2-yl)-2-nitroethyl)-2,5-dioxopyrrolidine-3-carboxylateC19H24N2O7[α]D25=+27.6 (c 3.7, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (S,S)
(R)-Methyl 1-butyl-3-((S)-1-(furan-2-yl)-2-nitroethyl)-2,5-dioxopyrrolidine-3-carboxylateC16H20N2O7[α]D24=-42 (c 1, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (R,S)
(S)-Methyl 1-butyl-3-((S)-1-(naphthalen-2-yl)-2-nitroethyl)-2,5-dioxopyrrolidine-3-carboxylateC22H24N2O6[α]D23=+2.0 (c 0.4, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (S,S)
(R)-Methyl 1-butyl-3-((S)-1-(naphthalen-2-yl)-2-nitroethyl)-2,5-dioxopyrrolidine-3-carboxylateC22H24N2O6[α]D=+30.0[α]D=+30.0 (c 0.2, CHCl3)Source of chirality: cinchonine and stereoselective synthesisAbsolute configuration: (R,S)
N-[(9R)-Cinchonan-9-yl]benzenesulfonamideC25H27N3O2S[α]D20=+67 (c 1.00, CHCl3)Source of chirality: cinchonineAbsolute configuration: (9R)
1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(9R)-cinchonan-9-yl]ureaC28H26F6N4O[α]D20=+134.0 (c 1.00, CHCl3)Source of chirality: cinchonineAbsolute configuration: (9R)
1-[(9R)-Cinchonan-9-yl]-3-(2-methoxyphenyl)thioureaC27H30N4OS[α]D25=+323 (c 0.08, CHCl3)Source of chirality: cinchonineAbsolute configuration: (9R)
1-[(9R)-Cinchonan-9-yl]-3-(3-methylphenyl)thioureaC27H30N4S[α]D25=+317 (c 0.11, CHCl3)Source of chirality: cinchonineAbsolute configuration: (9R)
1-[(9R)-Cinchonan-9-yl]-3-(4-nitrophenyl)thioureaC26H27N5O2S[α]D20=+216.7 (c 1.00, CHCl3)Source of chirality: cinchonineAbsolute configuration: (9R)
1-[(9R)-Cinchonan-9-yl]-3-(4-methoxyphenyl)thioureaC27H30N4OS[α]D24=+303.4 (c 1.30, CHCl3)Source of chirality: cinchonineAbsolute configuration: (9R)
1-[(9R)-Cinchonan-9-yl]-3-dodecylthioureaC32H48N4S[α]D25=+195 (c 0.12, CHCl3)Source of chirality: cinchonineAbsolute configuration: (9R)
