| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345354 | Tetrahedron: Asymmetry | 2014 | 6 Pages |
A novel chiral auxiliary containing a pyrrolidine ring has been utilised in the preparation of various chiral ketones with good to excellent enantioselectivities (up to 92%). It has been successfully employed in aldol and Michael reactions giving moderate to high selectivity.
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(S)-2-(Pyrrolidin-1-ylmethyl)pyrrolidin-1-amineC9H19N3[α]D20=-49.4 (c 1.08, EtOH)Source of chirality—commercially available (S)-N-(benzyloxycarbonyl)prolineAbsolute configuration: (S)
(S)-N-(Pentan-3-ylidine)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-amineC14H27N3[α]D20=+114 (c 1, EtOH)Source of chirality—commercially available (S)-N-(benzyloxycarbonyl)prolineAbsolute configuration: (S)
(S)-N-(1-Phenylpropylidene)-2-(pyrrolidin-lylmethyl)pyrrolidin-1-amineC18H27N3[α]D20=+418.5 (c 1.09, EtOH)Source of chirality—commercially available (S)-N-(benzyloxycarbonyl)prolineAbsolute configuration: (S)
(S)-N-(1-(4-Fluorophenyl)propylidene)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-amineC18H26FN3[α]D20=+289.6 (c 1, Et2O)Source of chirality—commercially available (S)-N-(benzyloxycarbonyl)prolineAbsolute configuration: (S)
(S)-N-(1-(4-Methoxyphenyl)propylidene)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-amineC19H29N3O[α]D20=+122.1 (c 0.6, Et2O)Source of chirality—commercially available (S)-N-(benzyloxycarbonyl)prolineAbsolute configuration: (S)
(S)-4-Methylnonan-3-oneC10H20OEe = 92%[α]D20=+5.5 (c 0.2, Et2O)Source of chirality—chiral auxiliaryAbsolute configuration: (S)
(4S,5R)-4-Methyl-6-nitro-5-phenylhexan-3-oneC13H17NO3Ee = 84%[α]D20=+3.5 (c 0.2, CHCl3)Source of chirality—chiral auxiliaryAbsolute configuration: (4S,5R)
