| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344744 | Tetrahedron: Asymmetry | 2010 | 8 Pages |
O-Benzyl-N-benzyloxymalimide 12 has been synthesized as a useful variant of the chiral building blocks 9. The advantage of the malimide 12 over 9 was demonstrated by mild and high-yielding reductive N-deprotection of N-benzyloxylactams 18a–i to give a series of (4R,5S)-5-alkyl-4-hydroxy-pyrrolidin-2-ones, which are key intermediates for the asymmetric synthesis of pyrrolidines, pyrrolizidines, and indolizidines, as well as β-hydroxy γ-amino acids. Lactam ent-11a has been applied to the synthesis of the mixed imide 25, a key intermediate for the total synthesis of microcolin B, which also demonstrated that lactam ent-11a or 11a can serve as a latent form of the 5-methyl-3-pyrrolin-2-one substructure of majusculamide D 4, deoxymajusculamide D, and the jamaicamides A–C.
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Diethyl (S)-2-(benzyloxy)succinateC15H20O5[α]D20=-59.9 (c 1.2, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (S)
Diethyl (R)-2-(benzyloxy)succinateC15H20O5[α]D20=+59.9 (c 1.0, CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (R)
(S)-2-(Benzyloxy)succinic acidC11H12O5[α]D20=-56.9 (c 1.9, CH3OH)Source of chirality: (S)-malic acidAbsolute configuration: (S)
(R)-2-(Benzyloxy)succinic acidC11H12O5[α]D20=+49.6 (c 1.2, CH3OH)Source of chirality: (R)-malic acidAbsolute configuration: (R)
(S)-1,3-Dibenzyloxypyrrolidin-2,5-dioneC18H17NO4[α]D20=-90.2 (c 1.0, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (S)
(R)-1,3-Dibenzyloxypyrrolidin-2,5-dioneC18H17NO4[α]D20=+90.0 (c 1.2, CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (R)
(4S,5R)-1,4-Dibenzyloxy-5-methylpyrrolidin-2-oneC19H21NO3[α]D20=+89.7 (c 1.0, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4R,5S)-1,4-Dibenzyloxy-5-methylpyrrolidin-2-oneC19H21NO3[α]D20=-95.5 (c 1.2, CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (4R,5S)
(4S,5R)-1,4-Dibenzyloxy-5-ethylpyrrolidin-2-oneC20H23NO3[α]D20=+86.8 (c 1.2, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-1,4-Dibenzyloxy-5-propylpyrrolidin-2-oneC21H25NO3[α]D20=+88.7 (c 1.0, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-1,4-Dibenzyloxy-5-isopropylpyrrolidin-2-oneC21H25NO3[α]D20=+69.5 (c 1.3, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-1,4-Dibenzyloxy-5-butylpyrrolidin-2-oneC22H27NO3[α]D20=+84.9 (c 1.0, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-1,4-Dibenzyloxy-5-isobutylpyrrolidin-2-oneC22H27NO3[α]D20=+90.7 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-1,4-Dibenzyloxy-5-heptylpyrrolidin-2-oneC25H33NO3[α]D20=+62.7 (c 0.6, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-1,4-Dibenzyloxy-5-octylpyrrolidin-2-oneC26H35NO3[α]D20=+64.3 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-1,4-Dibenzyloxy-5-phenylpyrrolidin-2-oneC24H23NO3[α]D20=+53.3 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-4-Benzyloxy-5-methylpyrrolidin-2-oneC12H15NO2[α]D20=+58.2 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4R,5S)-4-Benzyloxy-5-methylpyrrolidin-2-oneC12H15NO2[α]D20=-59.4 (c 1.2, CHCl3)Source of chirality: (R)-malic acidAbsolute configuration: (4R,5S)
(4S,5R)-4-Benzyloxy-5-ethylpyrrolidin-2-oneC13H17NO2[α]D20=+44.9 (c 1.5, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-4-Benzyloxy-5-ethylpyrrolidin-2-oneC14H19NO2[α]D20=+45.5 (c 2.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-4-Benzyloxy-5-isopropylpyrrolidin-2-oneC14H19NO2[α]D20=+42.6 (c 2.0, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-4-Benzyloxy-5-butylpyrrolidin-2-oneC15H21NO2[α]D20=+44.8 (c 1.2, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-4-Benzyloxy-5-isobutylpyrrolidin-2-oneC15H21NO2[α]D20=+47.8 (c 0.9, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-4-Benzyloxy-5-heptylpyrrolidin-2-oneC18H27NO2[α]D20=+39.3 (c 1.3, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-4-Benzyloxy-5-octylpyrrolidin-2-oneC19H29NO2[α]D20=+38.3 (c 1.3, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
(4S,5R)-4-Benzyloxy-5-phenylpyrrolidin-2-oneC17H17NO2[α]D20=+46.4 (c 2.2, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,5R)
1-tert-Butyl 2-perfluorophenyl (S)-pyrrolidine-1,2-dicarboxylateC16H16F5NO4[α]D20=-58 (c 1.2, CHCl3)Source of chirality: L-prolineAbsolute configuration: (S)
(4R,5S,1′S)-4-Benzyloxy-1-(N-butyloxycarbonylprolyl)-5-methylpyrrolidin-2-oneC22H30N2O5[α]D20=-49 (c 0.9, CHCl3)Source of chirality: (S)-malic acid and l-prolineAbsolute configuration: (4R,5S,1′S)
(4R,5S,1′S)-1-(N-butyloxycarbonylprolyl)-4-hydroxyl-5-methylpyrrolidin-2-oneC15H24N2O5[α]D20=-40.0 (c 1.3, CHCl3)Source of chirality: (S)-malic acid and l-prolineAbsolute configuration: (4R,5S,1′S)
(5S,1′S)-1-(N-Butyloxycarbonylprolyl)-5-methylpyrrol-2(5H)-oneC15H22N2O4[α]D20=-80 (c 1.0, CHCl3)Source of chirality: (S)-malic acid and l-prolineAbsolute configuration: (4R,5S,1′S)
