Diastereoselective nucleophilic addition of acetylide to N-benzyl-2, 3- O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)- and βhydroxy-α-amino acids

Tetrahedron Asymmetry

Volumn 8, Issue 20, 1997, Pages 3489-3496

  Merino, Pedro ^a   Franco, Santiago ^a   Merchan, Francisco L ^a   Tejero, Tomas ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; GLYCERALDEHYDE; HYDROXYACID;

OXIDATION; PRIORITY JOURNAL; PURIFICATION; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030691081     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00438-2     Document Type: Article

References (42)

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31. For previous uses of the ethynyl group as a carboxylic acid synthetic equivalent see: Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. Czernecki, S.; Franco, S.; Horns, S.; Valery. J.-M. Tetrahedron Lett. 1996, 37, 4003-4006. Czernecki, S.; Franco, S.; Valery, J.-M. J. Org. Chem 1997, 62, 4845-4847 and references cited therein. Interestingly, the vinyl group has also been used as a masked carboxyl group. See: Veeresha, G.; Datta, A. Tetrahedron Lett. 1997, 38, 5223-5224. Moody, C. J.; Lightfoot, A. P.; Gallagher, P. T. Synlett 1997, 659-660.
32. For previous uses of the ethynyl group as a carboxylic acid synthetic equivalent see: Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. Czernecki, S.; Franco, S.; Horns, S.; Valery. J.-M. Tetrahedron Lett. 1996, 37, 4003-4006. Czernecki, S.; Franco, S.; Valery, J.-M. J. Org. Chem 1997, 62, 4845-4847 and references cited therein. Interestingly, the vinyl group has also been used as a masked carboxyl group. See: Veeresha, G.; Datta, A. Tetrahedron Lett. 1997, 38, 5223-5224. Moody, C. J.; Lightfoot, A. P.; Gallagher, P. T. Synlett 1997, 659-660.
33. For previous uses of the ethynyl group as a carboxylic acid synthetic equivalent see: Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. Czernecki, S.; Franco, S.; Horns, S.; Valery. J.-M. Tetrahedron Lett. 1996, 37, 4003-4006. Czernecki, S.; Franco, S.; Valery, J.-M. J. Org. Chem 1997, 62, 4845-4847 and references cited therein. Interestingly, the vinyl group has also been used as a masked carboxyl group. See: Veeresha, G.; Datta, A. Tetrahedron Lett. 1997, 38, 5223-5224. Moody, C. J.; Lightfoot, A. P.; Gallagher, P. T. Synlett 1997, 659-660.
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40. The modifications consisted of: (i) no sodium bicarbonate was added to the reaction mixture; (ii) the reaction was finished in 2 min; and (iii) no sodium bisulfite was used in the work-up of the reaction. It is worth mentioning that under these conditions we did not observe oxidation of the N-benzyl group.
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