Documentation of a rare example of an intramolecular 1,2-addition of a trialkylborane to a carbonyl group

Tetrahedron Letters

Volumn 41, Issue 5, 2000, Pages 603-607

  Boeckman Jr , Robert K ^a   Mitchell, Lorna H ^a   Shao, Pengcheng ^a   Lachicotte, Rene J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; OXIDATION; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0343819998     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02165-6     Document Type: Article

References (15)

1. Only vinylboranes add to simple aldehydes: Jacob III, P.; Brown, H. C. J. Org. Chem. 1977, 42, 579-580.
2. (a) Sutherland, A. J.; Sutherland, J. K.; Crowley, P. J. J. Chem. Soc., Perkin Trans. 1 1996, 349-354;
3. (b) Snowden, R. L.; Brauchli, R.; Sonnay, P. Helv. Chim. Acta 1989, 72, 570-593;
4. (c) Zablocki, J. A.; Katzenellenbogen, J. A.; Carlson, K. E.; Norman, M. J.; Katzenellenbogen, B. S. J. Med. Chem. 1987, 30, 829-838;
5. (d) Snowden, R. L.; Sonnay, P. J. Org. Chem. 1984, 49, 1464-1465.
6. (a) Jung, M. E.; Siedem, C. S. J. Am. Chem. Soc. 1993, 115, 3822-3823;
7. (b) Ziegler, F. E.; Mencel, J. J. Tetrahedron Lett. 1983, 24, 1859-1862;
8. (c) Schultz, A. G.; Dittami, J. P.; Myong, S. O.; Sha, C. K. J. Am. Chem. Soc. 1983, 105, 3273-3279.
9. 3) 177.4, 156.6, 135.6 (4 signals), 133.8 (2 signals), 129.7 (2 signals), 127.4 (4 signals), 105.7, 89.3, 62.5, 50.3, 46.1, 40.0, 35.8, 33.5, 29.5, 28.4, 27.2, 26.9 (3 signals).
10. 3) 178.1, 152.9, 135.6 (4 signals), 133.9 (2 signals), 129.5 (2 signals), 127.6 (4 signals), 114.2, 81.3, 62.7, 52.1, 51.8, 48.6, 42.4, 37.8, 33.1, 32.0, 30.2, 27.4, 26.9 (3 signals), 26.2, 19.1, 16.0.
11. 2=9.99% (I>2σ). Coordinates have been deposited with the Cambridge Crystallographic Data Centre.
12. (a) Ardon-Jimenez, A.; Halsall, T. G. J. Chem. Soc., Perkin Trans. 1 1978, 1461-1470;
13. (b) Matteson, D. S. J. Organomet. Chem. 1981, 207, 13-65.
14. 11B NMR signals are broad (peak width (half height) ~160 Hz) resulting in an estimated detection limit of ~10%.
15. Miyaura, N.; Itoh, M.; Suzuki, A.; Brown, H. C.; Midland, M. M.; Jacob III, P. J. Amer. Chem. Soc. 1972, 94, 6549-6550.