Stereoselective SE2′ additions of enantioenriched allylic tin and indium reagents to protected threose and erythrose aldehydes: A general strategy for the stereocontrolled synthesis of precursors to the eight diastereomeric hexoses and their enantiomers

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 105-108

  Marshall, James A ^a   Hinkle, Kevin W ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002352889     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9640231     Document Type: Article

References (25)

1. For recent reviews, see: Marshall, J. A. Chemtracts: Org. Chem. 1992, 75. Yamamoto, Y.; Sheda, N. Advances in Detailed Reaction Mechanisms; JAI Press Inc.: Greenwich, CT, 1994; Vol. 3, pp 1-44. Marshall, J. A Chem. Rev., in press.
2. For recent reviews, see: Marshall, J. A. Chemtracts: Org. Chem. 1992, 75. Yamamoto, Y.; Sheda, N. Advances in Detailed Reaction Mechanisms; JAI Press Inc.: Greenwich, CT, 1994; Vol. 3, pp 1-44. Marshall, J. A Chem. Rev., in press.
3. For recent reviews, see: Marshall, J. A. Chemtracts: Org. Chem. 1992, 75. Yamamoto, Y.; Sheda, N. Advances in Detailed Reaction Mechanisms; JAI Press Inc.: Greenwich, CT, 1994; Vol. 3, pp 1-44. Marshall, J. A Chem. Rev., in press.
4. Marshall, J. A.; Welmaker, G. S.; Gung, B. W. J. Am. Chem. Soc. 1991, 113, 647 Marshall, J. A.; Jablonowski, J. A.; Elliott, L. M. J. Org. Chem. 1995, 60, 2662.
5. Marshall, J. A.; Welmaker, G. S.; Gung, B. W. J. Am. Chem. Soc. 1991, 113, 647 Marshall, J. A.; Jablonowski, J. A.; Elliott, L. M. J. Org. Chem. 1995, 60, 2662.
6. For previous work in this area, see: Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Boaretto, A.; Marton, D.; Taghavini, G. J. Organomet. Chem. 1985, 297, 149. Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1988, 110, 984. Keck, G E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136. Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067. Zschage, O.; Schwark, J-R.; Kramer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377. Thomas, E. J. Chemtracts: Org. Chem. 1994, 7, 207.
7. For previous work in this area, see: Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Boaretto, A.; Marton, D.; Taghavini, G. J. Organomet. Chem. 1985, 297, 149. Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1988, 110, 984. Keck, G E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136. Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067. Zschage, O.; Schwark, J-R.; Kramer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377. Thomas, E. J. Chemtracts: Org. Chem. 1994, 7, 207.
8. For previous work in this area, see: Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Boaretto, A.; Marton, D.; Taghavini, G. J. Organomet. Chem. 1985, 297, 149. Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1988, 110, 984. Keck, G E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136. Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067. Zschage, O.; Schwark, J-R.; Kramer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377. Thomas, E. J. Chemtracts: Org. Chem. 1994, 7, 207.
9. For previous work in this area, see: Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Boaretto, A.; Marton, D.; Taghavini, G. J. Organomet. Chem. 1985, 297, 149. Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1988, 110, 984. Keck, G E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136. Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067. Zschage, O.; Schwark, J-R.; Kramer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377. Thomas, E. J. Chemtracts: Org. Chem. 1994, 7, 207.
10. For previous work in this area, see: Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Boaretto, A.; Marton, D.; Taghavini, G. J. Organomet. Chem. 1985, 297, 149. Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1988, 110, 984. Keck, G E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136. Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067. Zschage, O.; Schwark, J-R.; Kramer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377. Thomas, E. J. Chemtracts: Org. Chem. 1994, 7, 207.
11. For previous work in this area, see: Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Boaretto, A.; Marton, D.; Taghavini, G. J. Organomet. Chem. 1985, 297, 149. Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1988, 110, 984. Keck, G E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136. Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067. Zschage, O.; Schwark, J-R.; Kramer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377. Thomas, E. J. Chemtracts: Org. Chem. 1994, 7, 207.
12. For previous work in this area, see: Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Boaretto, A.; Marton, D.; Taghavini, G. J. Organomet. Chem. 1985, 297, 149. Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1988, 110, 984. Keck, G E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136. Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067. Zschage, O.; Schwark, J-R.; Kramer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377. Thomas, E. J. Chemtracts: Org. Chem. 1994, 7, 207.
13. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920. The exact structure of this reagent is unknown. For some possibilities, see ref 5b.
14. For previous applications of allylic indium reagents, see: (a) Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M J. Org. Chem. 1993, 58, 5500. (b) Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538 and references cited therein.
15. For previous applications of allylic indium reagents, see: (a) Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M J. Org. Chem. 1993, 58, 5500. (b) Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538 and references cited therein.
16. Marshall, J. A.; Seletsky, B. M.; Luke, G. P. J. Org. Chem. 1994, 59, 3413.
17. For other approaches to carbohydrate homologation, see: McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. Damshefsky, S. J.; DeNinno, S. L.; Chen, S.; Boisvert, L.; Barbachyn, M. J. Am. Chem. Soc. 1989, 111, 5810. Ramza, J.; Zamojski, A Tetrahedron 1992, 48, 6123. Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4749. Casiraghi, G.; Rassu, G. Synthesis 1995, 607.
18. For other approaches to carbohydrate homologation, see: McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. Damshefsky, S. J.; DeNinno, S. L.; Chen, S.; Boisvert, L.; Barbachyn, M. J. Am. Chem. Soc. 1989, 111, 5810. Ramza, J.; Zamojski, A Tetrahedron 1992, 48, 6123. Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4749. Casiraghi, G.; Rassu, G. Synthesis 1995, 607.
19. For other approaches to carbohydrate homologation, see: McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. Damshefsky, S. J.; DeNinno, S. L.; Chen, S.; Boisvert, L.; Barbachyn, M. J. Am. Chem. Soc. 1989, 111, 5810. Ramza, J.; Zamojski, A Tetrahedron 1992, 48, 6123. Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4749. Casiraghi, G.; Rassu, G. Synthesis 1995, 607.
20. For other approaches to carbohydrate homologation, see: McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. Damshefsky, S. J.; DeNinno, S. L.; Chen, S.; Boisvert, L.; Barbachyn, M. J. Am. Chem. Soc. 1989, 111, 5810. Ramza, J.; Zamojski, A Tetrahedron 1992, 48, 6123. Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4749. Casiraghi, G.; Rassu, G. Synthesis 1995, 607.
21. For other approaches to carbohydrate homologation, see: McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 125. Damshefsky, S. J.; DeNinno, S. L.; Chen, S.; Boisvert, L.; Barbachyn, M. J. Am. Chem. Soc. 1989, 111, 5810. Ramza, J.; Zamojski, A Tetrahedron 1992, 48, 6123. Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4749. Casiraghi, G.; Rassu, G. Synthesis 1995, 607.
22. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
23. Reviews: Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 181-238. Kim, B. M.; Williams, S. P.; Masamune, S. Ibid. pp 239-275.
24. Reviews: Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 181-238. Kim, B. M.; Williams, S. P.; Masamune, S. Ibid. pp 239-275.
25. 3 at 300 MHz. For typical experimental protocols, see: Marshall, J. A ; Wang, X.-J. J. Org. Chem. 1991, 56, 960.