Acidic, selective monoacylation of vic-diols

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4469-4471

  Oikawa, Masato ^a   Wada, Akira ^a   Okazaki, Fumiaki ^a   Kusumoto, Shoichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000769453     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960081a     Document Type: Article

References (15)

1. For examples in natural product syntheses, see: (a) Nicolaou, K. C.; Ueno, H.; Liu, J.-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659. (b) Nicolaou, K. C.; Yue, E. W.; Naniwa, Y.; Riccardis, F. D.; Nadin, A.; Leresche, J. E.; Greca, S. L.; Yang, Z. Angew. Chem. Int. Ed. Engl. 1994, 33, 2184-2187. (c) Carreira, E. M.; Bois, J. D. J. Am. Chem. Soc. 1994, 116, 10825-10826. (d) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031. (e) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239-4243.
2. For examples in natural product syntheses, see: (a) Nicolaou, K. C.; Ueno, H.; Liu, J.-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659. (b) Nicolaou, K. C.; Yue, E. W.; Naniwa, Y.; Riccardis, F. D.; Nadin, A.; Leresche, J. E.; Greca, S. L.; Yang, Z. Angew. Chem. Int. Ed. Engl. 1994, 33, 2184-2187. (c) Carreira, E. M.; Bois, J. D. J. Am. Chem. Soc. 1994, 116, 10825-10826. (d) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031. (e) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239-4243.
3. For examples in natural product syntheses, see: (a) Nicolaou, K. C.; Ueno, H.; Liu, J.-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659. (b) Nicolaou, K. C.; Yue, E. W.; Naniwa, Y.; Riccardis, F. D.; Nadin, A.; Leresche, J. E.; Greca, S. L.; Yang, Z. Angew. Chem. Int. Ed. Engl. 1994, 33, 2184-2187. (c) Carreira, E. M.; Bois, J. D. J. Am. Chem. Soc. 1994, 116, 10825-10826. (d) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031. (e) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239-4243.
4. For examples in natural product syntheses, see: (a) Nicolaou, K. C.; Ueno, H.; Liu, J.-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659. (b) Nicolaou, K. C.; Yue, E. W.; Naniwa, Y.; Riccardis, F. D.; Nadin, A.; Leresche, J. E.; Greca, S. L.; Yang, Z. Angew. Chem. Int. Ed. Engl. 1994, 33, 2184-2187. (c) Carreira, E. M.; Bois, J. D. J. Am. Chem. Soc. 1994, 116, 10825-10826. (d) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031. (e) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239-4243.
5. For examples in natural product syntheses, see: (a) Nicolaou, K. C.; Ueno, H.; Liu, J.-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659. (b) Nicolaou, K. C.; Yue, E. W.; Naniwa, Y.; Riccardis, F. D.; Nadin, A.; Leresche, J. E.; Greca, S. L.; Yang, Z. Angew. Chem. Int. Ed. Engl. 1994, 33, 2184-2187. (c) Carreira, E. M.; Bois, J. D. J. Am. Chem. Soc. 1994, 116, 10825-10826. (d) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031. (e) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239-4243.
6. (a) Leigh, D. A.; Martin, R. P.; Smart, J. P.; Truscello, A. M. J. Chem. Soc., Chem. Commun. 1994, 1373-1374.
7. (b) McDougal, P. G.; Rico, J. G.; Oh, Y.-I.; Condon, B. D. J. Org. Chem. 1986, 51, 3388-3390.
8. (c) DeNinno, M. P.; Etienne, J. B.; Duplantier, K. C. Tetrahedron Lett. 1995, 36, 669-672.
9. (d) Nishiguchi, T.; Fujisaki, S.; Ishii, Y.; Yano, Y.; Nishida, A. J. Org. Chem. 1994, 59, 1191-1195 and references cited therein.
10. The cleavage of cyclic orthoesters by 80% aqueous AcOH in carbohydrate syntheses is the only example of this type of transformation. See: Hanessian, S.; Roy, R. Can. J. Chem. 1985, 63, 163-172 and references cited therein.
11. 3 toward the monoacetylation of gluco-, ribo-, and xylo-furanoses was reported. See: Bouchra, M.; Calinaud, P.; Gelas, J. Synthesis 1995, 561-565.
12. Oikawa, M.; Kusumoto, S. Tetrahedron: Asymmetry 1995, 6, 961-966.
13. 7 The reaction unequivocally includes IM2-type intermediates. From this work it is plausible that the cyclic IM2, rather than the opened IM1, is also the intermediate in the present acylation of the ethylene glycol-derived orthoester (entry 14 in Table 1). (Matrix Presented)
14. Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215-8216.
15. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547 and references cited therein.