Use of bis-(chiral α-methylbenzyl)glycine esters for synthesis of enantiopure β-hydroxyamino esters

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3305-3308

  Yamashita, Ayako ^a   Norton, Emily B ^a   Williamson, R Thomas ^a   Ho, Douglas M ^a,b   Sinishtaj, Sandra ^a   Mansour, Tarek S ^a  

^a WYETH RESEARCH   (United States)

^b PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ANTIBIOTIC AGENT; ESTER; GLYCINE DERIVATIVE; HYDROXYAMINO ACID; MURAYMYCIN; RIBOSYLGLYCINE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS;

ALDEHYDES; ANTI-BACTERIAL AGENTS; CRYSTALLOGRAPHY, X-RAY; ESTERS; GLYCINE; HYDROXAMIC ACIDS; MOLECULAR STRUCTURE; NUCLEOTIDES; PEPTIDES; PEPTIDOGLYCAN; STEREOISOMERISM; UREA;

EID: 0141856223     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030085j     Document Type: Article

References (50)

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2. Biological activity of muraymycins and their analogues: (a) Singh, G.; Yang, Y.; Rasmussen, B. A.; Petersen, P. J.; McDonald, L. A.; Yamashita, A.; Lin, Y.-I.; Norton, E.; Francisco, G. D.; Li, Z.; Barbieri, L. R. The 41st Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago, IL; Abstract 1163; December 16-19, 2001. (b) Lin, Y.-I.; Li, Z.; Francisco, G. D.; McDonald, L. A.; Davis, R. A.; Singh, G.; Yang, Y.; Mansour, T. S. Bioorg. Med. Chem. Lett. 2002, 12, 2341. (c) Yamashita, A.; Norton, E.; Petersen, P. J.; Rasmussen, B. A.; Singh, G.; Yang, Y.; Mansour, T. S.; Ho, D. M. Bioorg. Med. Chem. Lett. 2003, 13, in press, and other references therein.
3. Biological activity of muraymycins and their analogues: (a) Singh, G.; Yang, Y.; Rasmussen, B. A.; Petersen, P. J.; McDonald, L. A.; Yamashita, A.; Lin, Y.-I.; Norton, E.; Francisco, G. D.; Li, Z.; Barbieri, L. R. The 41st Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago, IL; Abstract 1163; December 16-19, 2001. (b) Lin, Y.-I.; Li, Z.; Francisco, G. D.; McDonald, L. A.; Davis, R. A.; Singh, G.; Yang, Y.; Mansour, T. S. Bioorg. Med. Chem. Lett. 2002, 12, 2341. (c) Yamashita, A.; Norton, E.; Petersen, P. J.; Rasmussen, B. A.; Singh, G.; Yang, Y.; Mansour, T. S.; Ho, D. M. Bioorg. Med. Chem. Lett. 2003, 13, in press, and other references therein.
4. Isolation and structure determination of muraymycins: McDonald, L. A.; Barbieri, L. R.; Carter, G. T.; Lenoy, E.; Petersen, P. P.; Siegel, M. M.; Sign, G.; Williamson, R. T. J. Am. Chem. Soc. 2002, 124, 10260.
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15. Preparation of 4a and use of 4a for aldol and Michael reactions, etc.: (a) Scolastico, C. Tetrahedron Lett. 1987, 43, 2317. (b) Gray, B. D.; Jeffs, P. W. J. Chem. Soc., Chem. Commun. 1987, 1329. (c) Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. (d) Elder, T.; Gregory, L. C.; Orozco, A.; Pflug, J. L.; Wiens, P. S.; Wilkinson, T. J. Synth. Commun. 1989, 19, 763. (e) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377.
16. Preparation of 4a and use of 4a for aldol and Michael reactions, etc.: (a) Scolastico, C. Tetrahedron Lett. 1987, 43, 2317. (b) Gray, B. D.; Jeffs, P. W. J. Chem. Soc., Chem. Commun. 1987, 1329. (c) Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. (d) Elder, T.; Gregory, L. C.; Orozco, A.; Pflug, J. L.; Wiens, P. S.; Wilkinson, T. J. Synth. Commun. 1989, 19, 763. (e) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377.
17. Preparation of 4a and use of 4a for aldol and Michael reactions, etc.: (a) Scolastico, C. Tetrahedron Lett. 1987, 43, 2317. (b) Gray, B. D.; Jeffs, P. W. J. Chem. Soc., Chem. Commun. 1987, 1329. (c) Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. (d) Elder, T.; Gregory, L. C.; Orozco, A.; Pflug, J. L.; Wiens, P. S.; Wilkinson, T. J. Synth. Commun. 1989, 19, 763. (e) Yamaguchi, M.; Torisu, K.; Minami, T. Chem. Lett. 1990, 377.
18. Crystals of 7a suitable for X-ray were obtained as colorless prisms from ether/hexanes. Crystals of the para-nitrophenyl urea derivative 9a of 8a were obtained as yellow prisms from methylene chloride/MeOH. The supplementary publication numbers for the X-ray data are CCDC 214437 for 7a and CCDC 214438 for 9a.
19. Banfi, L.; Cardani, S.; Potenza, D.; Scolastico, C. Tetrahedron 1987, 43, 2317. Other glycine esters 4c-f were prepared from ethyl bromoacetate and appropriate chiral dibeznylamine derivatives.
20. Relative stereochemistry of 5b and 6b was determined by NMR spectroscopy through implementation of the J-configuration analysis method: (a) Matsumori, N.; Kaneno, D.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866. (b) Williamson, R. T.; Marquez, B. L.; Barrios Sosa, A. C.; Koehn, F. K. Magn. Reson. Chem. 2003, 41, 379. This technique was used for the structure determination of muraymycins: see ref 2.
21. Relative stereochemistry of 5b and 6b was determined by NMR spectroscopy through implementation of the J-configuration analysis method: (a) Matsumori, N.; Kaneno, D.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866. (b) Williamson, R. T.; Marquez, B. L.; Barrios Sosa, A. C.; Koehn, F. K. Magn. Reson. Chem. 2003, 41, 379. This technique was used for the structure determination of muraymycins: see ref 2.
22. 1H NMR spectra and TLC analyses.
23. (a)Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1995, 6, 1741.
24. (b) Belokon, Y. N.; Kochetkov, K. A.; Ikonnikov, N. S.; Strelkova, T. V. ; Harutyunyan, S. R.; Saghiyan, A. S. Tetrahedron: Asymmetry 2001, 12, 481.
25. 1H NMR spectra and optical rotations of these free amino esters were used for further confirmation of their stereochemistry.
26. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
27. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
28. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
29. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
30. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
31. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
32. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
33. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
34. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
35. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (1) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
36. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (l) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
37. Syntheses of β-hydroxy-leucines have been reported: (a) Jung, M. E. ; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (b) Hale, K. J.; Manaviazar, S. ; Delisser, V. M. Tetrahedron 1994, 50, 9181. (c) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584. (e) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am, Chem. Soc. 1997, 119, 11734. (f) Laib, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771. (g) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709. (h) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382. (i) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 664. (j) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (k) Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757. (l) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883.
38. Structures of compounds 11c and 10d were determined by their X-ray analyses. Crystals suitable for 11c were obtained as colorless prisms from ether/hexanes (supplementary publication number CCDC 214440). Crystals suitable for 10d were also obtained as colorless prisms from ether/hexanes (supplementary publication number CCDC 214439).
39. We assumed that the (2S,3S)-diastereomer 10e was the major component, along with the (2R,3R)-isomer 11e as the second major component. Related references: (a) Suga, H.; Ikai, K.; Ibata, T. J. Org. Chem. 1999, 64, 7040. (b) Tomasini, C.; Vecchione, A. Org. Lett. 1999, 1, 2153. (c) Markovic, D.; Hamersak, Z.; Visnjevac, A.; Kojic-Prodic, B.; Sunjic, V. Helv. Chem. Acta 2000, 83, 603. (d) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo. P. J. Org. Chem. 2000, 65, 7663 and other references therein.
40. We assumed that the (2S,3S)-diastereomer 10e was the major component, along with the (2R,3R)-isomer 11e as the second major component. Related references: (a) Suga, H.; Ikai, K.; Ibata, T. J. Org. Chem. 1999, 64, 7040. (b) Tomasini, C.; Vecchione, A. Org. Lett. 1999, 1, 2153. (c) Markovic, D.; Hamersak, Z.; Visnjevac, A.; Kojic-Prodic, B.; Sunjic, V. Helv. Chem. Acta 2000, 83, 603. (d) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo. P. J. Org. Chem. 2000, 65, 7663 and other references therein.
41. We assumed that the (2S,3S)-diastereomer 10e was the major component, along with the (2R,3R)-isomer 11e as the second major component. Related references: (a) Suga, H.; Ikai, K.; Ibata, T. J. Org. Chem. 1999, 64, 7040. (b) Tomasini, C.; Vecchione, A. Org. Lett. 1999, 1, 2153. (c) Markovic, D.; Hamersak, Z.; Visnjevac, A.; Kojic-Prodic, B.; Sunjic, V. Helv. Chem. Acta 2000, 83, 603. (d) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo. P. J. Org. Chem. 2000, 65, 7663 and other references therein.
42. We assumed that the (2S,3S)-diastereomer 10e was the major component, along with the (2R,3R)-isomer 11e as the second major component. Related references: (a) Suga, H.; Ikai, K.; Ibata, T. J. Org. Chem. 1999, 64, 7040. (b) Tomasini, C.; Vecchione, A. Org. Lett. 1999, 1, 2153. (c) Markovic, D.; Hamersak, Z.; Visnjevac, A.; Kojic-Prodic, B.; Sunjic, V. Helv. Chem. Acta 2000, 83, 603. (d) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo. P. J. Org. Chem. 2000, 65, 7663 and other references therein.
43. Crystals of 6e suitable for X-ray were obtained as colorless prisms from ether/hexanes. The supplementary publication number for the X-ray for 6e is CCDC 214436.
44. Stereochemical outcome of the lithium enolate geometry of substituted esters in various solvent systems has been reported: (a) Jeffery, E. A.; Meisters, A.; Mole, T. J. Organomet. Chem. 1974, 74, 373. (b) Dubois, J. E.; Fellman, P. Tetrahedron Lett. 1975, 16, 1225. (c) Ireland, R. E.; Willard, A. K. Tetrahedron Lett. 1975, 16, 3975. (d) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. (e) Ireland, R. E.; Thaisrivongs, S.; Vanier, N.; Wilcox, C. S. J. Org. Chem. 1980, 45, 48 and other references therein.
45. Stereochemical outcome of the lithium enolate geometry of substituted esters in various solvent systems has been reported: (a) Jeffery, E. A.; Meisters, A.; Mole, T. J. Organomet. Chem. 1974, 74, 373. (b) Dubois, J. E.; Fellman, P. Tetrahedron Lett. 1975, 16, 1225. (c) Ireland, R. E.; Willard, A. K. Tetrahedron Lett. 1975, 16, 3975. (d) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. (e) Ireland, R. E.; Thaisrivongs, S.; Vanier, N.; Wilcox, C. S. J. Org. Chem. 1980, 45, 48 and other references therein.
46. Stereochemical outcome of the lithium enolate geometry of substituted esters in various solvent systems has been reported: (a) Jeffery, E. A.; Meisters, A.; Mole, T. J. Organomet. Chem. 1974, 74, 373. (b) Dubois, J. E.; Fellman, P. Tetrahedron Lett. 1975, 16, 1225. (c) Ireland, R. E.; Willard, A. K. Tetrahedron Lett. 1975, 16, 3975. (d) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. (e) Ireland, R. E.; Thaisrivongs, S.; Vanier, N.; Wilcox, C. S. J. Org. Chem. 1980, 45, 48 and other references therein.
47. Stereochemical outcome of the lithium enolate geometry of substituted esters in various solvent systems has been reported: (a) Jeffery, E. A.; Meisters, A.; Mole, T. J. Organomet. Chem. 1974, 74, 373. (b) Dubois, J. E.; Fellman, P. Tetrahedron Lett. 1975, 16, 1225. (c) Ireland, R. E.; Willard, A. K. Tetrahedron Lett. 1975, 16, 3975. (d) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. (e) Ireland, R. E.; Thaisrivongs, S.; Vanier, N.; Wilcox, C. S. J. Org. Chem. 1980, 45, 48 and other references therein.
48. Stereochemical outcome of the lithium enolate geometry of substituted esters in various solvent systems has been reported: (a) Jeffery, E. A.; Meisters, A.; Mole, T. J. Organomet. Chem. 1974, 74, 373. (b) Dubois, J. E.; Fellman, P. Tetrahedron Lett. 1975, 16, 1225. (c) Ireland, R. E.; Willard, A. K. Tetrahedron Lett. 1975, 16, 3975. (d) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. (e) Ireland, R. E.; Thaisrivongs, S.; Vanier, N.; Wilcox, C. S. J. Org. Chem. 1980, 45, 48 and other references therein.
49. A directing effect of neighboring aromatic groups on the regiochemistry of formation and on the stereochemistry of alkylation of lithium enolates has been suggested: Posner, G. H.; Lentz, C. M. J. Am. Chem. Soc. 1979, 101, 934. Other references therein.
50. Crystallographic data for the compounds in this manuscript, which were analyzed by X-ray, have been deposited at the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EW, UK. The supplementary publication number for X-ray data for each compound is individually listed in the footnote.