Synthesis of Chiral α,δ-Dioxygenated Allylic Stannanes as Reagents for Carbohydrate Synthesis and Homologation

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8732-8738

  Marshall, James A ^a   Garofalo, Albert W ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003374057     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961671b     Document Type: Article

References (16)

1. Marshall, J. A. Chem. Rev. 1996, 96, 31.
2. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
3. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 105.
4. 1 equation presented
5. McDougal, P. M.; Rico, J. G.; Oh, Y. I.; Condon, B. D. J. Org. Chem. 1986, 57, 3388.
6. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647.
7. Marshall, J. A.; Welmaker, G. S. J. Org. Chem. 1992, 57, 7158.
8. Marshall, J. A.; Jablonowski, J. A.; Elliott, L. M. J. Org. Chem. 1995, 60, 2662.
9. Landmann, B.; Hoffman, R. W. Chem. Ber. 1987, 720, 331.
10. Isaac, M. B.; Chan, T.-H. Tetrahedron Lett. 1995, 36, 8957.
11. E2′ process and the subsequent isomerization (ii -iii) occurs with syn stereochemistry. Cf.: Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995,60, 5550. The indium intermediates are most likely unsymmetrical Cl-bridged dimers but are depicted as monomers to simplify the analysis. equation presentation
12. A reviewer has suggested that syn adducts may arise via a noncyclic transition state in which InCla is coordinated to the aldehyde carbonyl. Because of their increased basicity, enals would be more likely to follow this pathway. A similar explanation has been advanced to account for the formation of anti aldol adducts from the reaction of /5-SPh enals and aromatic aldehydes with the BuaBOTf-derived boron enolate of a chiral N-propionyloxazolidinone: Danda, H.; Hansen, M. M-; Heathcock, C. H. J. Org. Chem. 1990, 55, 173. This point will be addressed in a future study with allylic indium intermediates in which E/Z isomerism is not an issue.
13. This hexose is listed at $799.50/g in the 1996 Aldrich Catalog (Aldrich No. 86,226-6): Aldrich Catalog Handbook of Fine Chemicals; Aldrich Chemical Co.: Milwaukee, WI.
14. Marshall, J. A.; Welmaker, G. S.; Gung, B. W. J. Am. Chem. Soc. 1991, 113, 647.
15. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973.
16. 3.