Preparation of alcohols from sulfones and trialkylboranes

Tetrahedron Letters

Volumn 44, Issue 24, 2003, Pages 4451-4454

  Billaud, Célia ^a   Goddard, Jean Philippe ^a   Le Gall, Thierry ^a   Mioskowski, Charles ^a,b  

^a CEA SACLAY   (France)

^b CNRS   (France)

Author keywords

Alcohol; Borane; Boron compound; Sulfone

Indexed keywords

ALCOHOL DERIVATIVE; BORANE DERIVATIVE; BORON DERIVATIVE; DIMETHYL SULFIDE; HYDROPEROXIDE; SULFONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; HYDROBORATION; ISOMERISM; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS;

EID: 0038066122     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01025-6     Document Type: Article

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11. See, for example: (a) Tufariello, J. J.; Lee, L. T. C. J. Am. Chem. Soc. 1966, 88, 4757-4759; (b) Tufariello, J. J.; Wojtkowski, P.; Lee, L. T. C. J. Chem. Soc., Chem. Commun. 1967, 505-506; (c) Matteson, D. S.; Majumbar, D. J. Am. Chem. Soc. 1980, 102, 7588-7590; (d) Truce, W. E.; Mura, L. A.; Smith, P. J.; Young, F. J. Org. Chem. 1974, 39, 1449-1450; (e) Hooz, J.; Linke, S. J. Am. Chem. Soc. 1968, 90, 5936-5937; (f) Pasto, D. J.; Wojtkowski, P. W. Tetrahedron Lett. 1970, 215-218; (g) Kabalka, G. W.; Maddox, J. T.; Bogas, E. J. Org. Chem. 1994, 59, 5530-5531; (h) Goddard, J.-P.; Le Gall, T.; Mioskowski, C. Org. Lett. 2000, 2, 1455-1456.
12. See, for example: (a) Tufariello, J. J.; Lee, L. T. C. J. Am. Chem. Soc. 1966, 88, 4757-4759; (b) Tufariello, J. J.; Wojtkowski, P.; Lee, L. T. C. J. Chem. Soc., Chem. Commun. 1967, 505-506; (c) Matteson, D. S.; Majumbar, D. J. Am. Chem. Soc. 1980, 102, 7588-7590; (d) Truce, W. E.; Mura, L. A.; Smith, P. J.; Young, F. J. Org. Chem. 1974, 39, 1449-1450; (e) Hooz, J.; Linke, S. J. Am. Chem. Soc. 1968, 90, 5936-5937; (f) Pasto, D. J.; Wojtkowski, P. W. Tetrahedron Lett. 1970, 215-218; (g) Kabalka, G. W.; Maddox, J. T.; Bogas, E. J. Org. Chem. 1994, 59, 5530-5531; (h) Goddard, J.-P.; Le Gall, T.; Mioskowski, C. Org. Lett. 2000, 2, 1455-1456.
13. See, for example: (a) Tufariello, J. J.; Lee, L. T. C. J. Am. Chem. Soc. 1966, 88, 4757-4759; (b) Tufariello, J. J.; Wojtkowski, P.; Lee, L. T. C. J. Chem. Soc., Chem. Commun. 1967, 505-506; (c) Matteson, D. S.; Majumbar, D. J. Am. Chem. Soc. 1980, 102, 7588-7590; (d) Truce, W. E.; Mura, L. A.; Smith, P. J.; Young, F. J. Org. Chem. 1974, 39, 1449-1450; (e) Hooz, J.; Linke, S. J. Am. Chem. Soc. 1968, 90, 5936-5937; (f) Pasto, D. J.; Wojtkowski, P. W. Tetrahedron Lett. 1970, 215-218; (g) Kabalka, G. W.; Maddox, J. T.; Bogas, E. J. Org. Chem. 1994, 59, 5530-5531; (h) Goddard, J.-P.; Le Gall, T.; Mioskowski, C. Org. Lett. 2000, 2, 1455-1456.
14. See, for example: (a) Tufariello, J. J.; Lee, L. T. C. J. Am. Chem. Soc. 1966, 88, 4757-4759; (b) Tufariello, J. J.; Wojtkowski, P.; Lee, L. T. C. J. Chem. Soc., Chem. Commun. 1967, 505-506; (c) Matteson, D. S.; Majumbar, D. J. Am. Chem. Soc. 1980, 102, 7588-7590; (d) Truce, W. E.; Mura, L. A.; Smith, P. J.; Young, F. J. Org. Chem. 1974, 39, 1449-1450; (e) Hooz, J.; Linke, S. J. Am. Chem. Soc. 1968, 90, 5936-5937; (f) Pasto, D. J.; Wojtkowski, P. W. Tetrahedron Lett. 1970, 215-218; (g) Kabalka, G. W.; Maddox, J. T.; Bogas, E. J. Org. Chem. 1994, 59, 5530-5531; (h) Goddard, J.-P.; Le Gall, T.; Mioskowski, C. Org. Lett. 2000, 2, 1455-1456.
15. See, for example: (a) Tufariello, J. J.; Lee, L. T. C. J. Am. Chem. Soc. 1966, 88, 4757-4759; (b) Tufariello, J. J.; Wojtkowski, P.; Lee, L. T. C. J. Chem. Soc., Chem. Commun. 1967, 505-506; (c) Matteson, D. S.; Majumbar, D. J. Am. Chem. Soc. 1980, 102, 7588-7590; (d) Truce, W. E.; Mura, L. A.; Smith, P. J.; Young, F. J. Org. Chem. 1974, 39, 1449-1450; (e) Hooz, J.; Linke, S. J. Am. Chem. Soc. 1968, 90, 5936-5937; (f) Pasto, D. J.; Wojtkowski, P. W. Tetrahedron Lett. 1970, 215-218; (g) Kabalka, G. W.; Maddox, J. T.; Bogas, E. J. Org. Chem. 1994, 59, 5530-5531; (h) Goddard, J.-P.; Le Gall, T.; Mioskowski, C. Org. Lett. 2000, 2, 1455-1456.
16. See, for example: (a) Tufariello, J. J.; Lee, L. T. C. J. Am. Chem. Soc. 1966, 88, 4757-4759; (b) Tufariello, J. J.; Wojtkowski, P.; Lee, L. T. C. J. Chem. Soc., Chem. Commun. 1967, 505-506; (c) Matteson, D. S.; Majumbar, D. J. Am. Chem. Soc. 1980, 102, 7588-7590; (d) Truce, W. E.; Mura, L. A.; Smith, P. J.; Young, F. J. Org. Chem. 1974, 39, 1449-1450; (e) Hooz, J.; Linke, S. J. Am. Chem. Soc. 1968, 90, 5936-5937; (f) Pasto, D. J.; Wojtkowski, P. W. Tetrahedron Lett. 1970, 215-218; (g) Kabalka, G. W.; Maddox, J. T.; Bogas, E. J. Org. Chem. 1994, 59, 5530-5531; (h) Goddard, J.-P.; Le Gall, T.; Mioskowski, C. Org. Lett. 2000, 2, 1455-1456.
17. See, for example: (a) Tufariello, J. J.; Lee, L. T. C. J. Am. Chem. Soc. 1966, 88, 4757-4759; (b) Tufariello, J. J.; Wojtkowski, P.; Lee, L. T. C. J. Chem. Soc., Chem. Commun. 1967, 505-506; (c) Matteson, D. S.; Majumbar, D. J. Am. Chem. Soc. 1980, 102, 7588-7590; (d) Truce, W. E.; Mura, L. A.; Smith, P. J.; Young, F. J. Org. Chem. 1974, 39, 1449-1450; (e) Hooz, J.; Linke, S. J. Am. Chem. Soc. 1968, 90, 5936-5937; (f) Pasto, D. J.; Wojtkowski, P. W. Tetrahedron Lett. 1970, 215-218; (g) Kabalka, G. W.; Maddox, J. T.; Bogas, E. J. Org. Chem. 1994, 59, 5530-5531; (h) Goddard, J.-P.; Le Gall, T.; Mioskowski, C. Org. Lett. 2000, 2, 1455-1456.
18. Uguen D. Bull. Soc. Chim. Fr. II. 1981;99-102.
19. Simpkins N.S. Sulphones in Organic Synthesis. 1993;Pergamon Press, Oxford.
20. 3) δ 137.6, 130.4, 129.9, 126.2, 72.4, 47.9, 41.8, 31.8, 29.8, 26.3, 23.9, 22.5, 13.9.
21. 3) δ 141.6, 129.1, 128.0, 125.5, 63.0, 43.7, 36.6, 34.9, 32.7, 29.6, 27.0, 25.7, 19.4.