| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348647 | Tetrahedron: Asymmetry | 2006 | 6 Pages |
Direct catalytic enantio- and diastereoselective Michael addition reaction of aldehydes to nitrostyrenes is described using a series of recyclable chiral 2-trimethylsilanyloxy-methyl-pyrrolidine-based dendritic catalysts. Good yields (up to 82%), and high diastereoselectivities (up to syn/anti = 95/5) and enantioselectivities (up to 99% ee) have been obtained.
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(2R,3S)-2-Isopropyl-4-nitro-3-phenylbutanalC13H17NO3Ee = 99%[α]D24.3=+53.1 (c 0.77, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (2R,3S)
(2R,3S)-3-(4-Bromophenyl)-2-isopropyl-4-nitrobutanalC13H16BrNO3Ee = 99%[α]D22.2=+36.2 (c 1.60, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (2R,3S)
(2R,3S)-2-Isopropyl-3-(naphthalen-1-yl)-4-nitrobutanalC17H19NO3Ee = 99%[α]D22.5=+49.5 (c 0.45, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (2R,3S)
(2R,3S)-2-Methyl-4-nitro-3-phenylbutanalC11H13NO3Ee = 99%[α]D22.3=+29.7 (c 1.00, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (2R,3S)
(2R,3S)-2-Ethyl-4-nitro-3-phenylbutanalC12H15NO3Ee = 99%[α]D23.7=+59.6 (c 0.60, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (2R,3S)
(R)-2-((S)-2-Nitro-1-phenylethyl)pentanalC13H17NO3Ee = 97%[α]D23.8=+69.1 (c 0.60, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (2R,3S)
(R)-2((S)-1-(4-Methoxyphenyl)-2-nitroethyl)pentanalC14H19NO4Ee = 99%[α]D24.1=+47.2 (c 1.30, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (2R,3S)
(R)-2-((S)-2-Nitro-1-phenylethyl)hexanalC14H19NO3Ee = 99%[α]D24.6=+35.5 (c 1.05, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (2R,3S)
(R)-2-((S)-2-Nitro-1-phenylethyl)heptanalC15H21NO3Ee = 99%[α]D24.0=+34.1 (c 2.35, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (2R,3S)
(R)-2,2-Dimethyl-4-nitro-3-phenylbutanalC12H14BrNO3Ee = 89%[α]D21.5=+5.6 (c 1.00, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (R)
(R)-3-(4-Bromophenyl)-2,2-dimethyl-4-nitrobutanalC12H14BrNO3Ee = 77%[α]D24.1=+8.1 (c 0.60, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (R)
