Synthesis of nonracemic β-hydroxy ketones and carbonate derivatives from homopropargylic alcohols through iodolactonization

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 3798-3799

  Marshall, James A ^a   Yanik, Mathew M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYKETONE; ALCOHOL; CARBONIC ACID; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; COMPLEX FORMATION; HYDROLYSIS; RACEMIC MIXTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033612217     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990439d     Document Type: Article

References (18)

1. (a) Marshall, J. A.; Perkins, J. F.; Wolf, M. A. J. Org. Chem. 1996, 60, 5556.
2. (b) Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1997, 62, 6001.
3. (c) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812.
4. (d) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696.
5. Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1998, 63, 4381. Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 817. Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
6. Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1998, 63, 4381. Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 817. Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
7. Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1998, 63, 4381. Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 817. Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
8. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.6. Evans, D. A. Aldrichimica Acta 1982, 15, 23.
9. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.6. Evans, D. A. Aldrichimica Acta 1982, 15, 23.
10. Paterson, I.; Scott, J. P. Tetrahedron Lett. 1997, 38, 7441. Review: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
11. Paterson, I.; Scott, J. P. Tetrahedron Lett. 1997, 38, 7441. Review: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
12. (a) Brown, H. C.; Kurek, J. T.; Rei, M. H.; Thompson, K. L. J. Org. Chem. 1984, 49, 2551.
13. (b) Overman, L. E.; Campbell, C. B. J. Org. Chem. 1974, 39, 1474
14. Duan, J. J.-W.; Smith, A. B. J. Org. Chem. 1893, 58, 3703. Bongeni, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1882, 47, 4626.
15. Duan, J. J.-W.; Smith, A. B. J. Org. Chem. 1893, 58, 3703. Bongeni, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1882, 47, 4626.
16. Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143.
17. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141.
18. The (S), (R), and racemic forms are available from the Aldrich Chemical Co., Inc., Milwaukee, WI.