Efficient enantioselective synthesis of (2R,3R)- and (2S,3S)-3-hydroxyleucines and their diastereomers through dynamic kinetic resolution

Author:

Makino Kazuishi,Okamoto Naoki,Hara Osamu,Hamada Yasumasa

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference8 articles.

1. Papuamides A−D, HIV-Inhibitory and Cytotoxic Depsipeptides from the Sponges Theonella mirabilis and Theonella swinhoei Collected in Papua New Guinea

2. Polyoxypeptins A and B Produced by Streptomyces:  Apoptosis-Inducing Cyclic Depsipeptides Containing the Novel Amino Acid (2S,3R)-3-Hydroxy-3-methylproline

3. For the synthesis of (2R,3R)- and (2S,3S)-3-hydroxyleucines, see: (a) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34–36; (b) Corey, E. J.; Lee, D. H.; Choi, S. Tetrahedron Lett. 1992, 33, 6735–6738; (c) Kanemasa, S.; Mori, T.; Tatsukawa, A. Tetrahedron Lett. 1993, 34, 8293–8296; (d) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181–9188; (e) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, III, A. B. J. Am. Chem. Soc. 1996, 118, 3584–3590; (f) Williams, L.; Zhang, Z.; Shao, F.; Carroll, P. J.; Joulliè, M. M. Tetrahedron 1996, 52, 11673–11694; (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709–1713; (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382–2384; (i) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843–3846; (j) Adams, Z. M.; Jackson, R. F. W.; Palmer, N. J.; Rami, H. K.; Wythes, M. J. J. Chem. Soc., Perkin Trans. 1 1999, 937–947.

4. For the synthesis of (2R,3S)- and (2S,3R)-3-hydroxyleucines, see: (a) Jung, M. E.; Yung, Y. H. Tetrahedron Lett. 1989, 30, 6637–6640; (b) Panek, J. S.; Masse, C. E. Angew. Chem., Int. Ed. 1999, 38, 1093–1095; (c) Soucy, F.; Grenier, L.; Behnke, M. L.; Destree, A. T.; McCormack, T. A.; Adams, J.; Plamondon, L. J. Am. Chem. Soc. 1999, 121, 9967–9976; (d) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663–7666. See also references 3e and 3f.

5. Stereoselective Organic Synthesis via Dynamic Kinetic Resolution

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