Boron-mediated stereoselective syntheses of γ,γ-disubstituted allenamides

Journal of Organic Chemistry

Volumn 70, Issue 21, 2005, Pages 8628-8630

  Hyland, Christopher J T ^a   Hegedus, Louis S ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMINES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALLENAMIDES; DISTEREOSELECTIVITY; N-PROPARGYLOXAZOLIDINONES; STEREOSELECTIVE SYNTHESIS;

BORON;

ALDEHYDE; AMIDE; BORANE DERIVATIVE; BORON DERIVATIVE; ORGANOMETALLIC COMPOUND; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

ALKADIENES; AMIDES; BORON COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 26844453978     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051385c     Document Type: Article

References (19)

1. For a review on propargyl and allenyl organometallics, see: Yamamoto, H. Propargyl and Allenyl Organometallics. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: London, 1991; Vol. 2, pp 81-98.
2. Hoppe, D.; Gonschorrek, C.; Schmidt, D.; Egert, E. Tetrahedron 1987, 43, 2457.
3. Ranslow, P. B. D.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105.
4. For a review on allenamides in organic synthesis, see: Wei, L.-L.; Xiong, H.; Hsung, R. P. Acc. Chem. Res. 2003, 36, 773.
5. (a) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
6. (b) Tanaka, H.; Kameyama, Y.; Sumida, S.; Yamada, T.; Tokumaru, Y.; Shiroi, T.; Sasaoka, M.; Taniguchi, M.; Torri, S. Synlett 1991, 888.
7. (c) Farina, V.; Kant, J. Tetrahedron Lett. 1996, 33, 3559.
8. (d) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339.
9. (e) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241.
10. Marshall, J. A.; Yanik, M. M. J. Org. Chem. 2001, 66, 1373,
11. (a) Wang, K. K.; Wang, Z.; Gu, Y. G. Tetrahedron Lett. 1993, 34, 8391.
12. (b) Wang, K. K.; Wang, Z.; Sattsangi, P. D. J. Org. Chem. 1996, 61, 1516.
13. Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376.
14. For reviews, see: (a) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12.
15. (b) Ma, S. Acc. Chem. Res. 2003, 36, 701.
16. Brummond, K. M.; Chen, H.; Mitasev, B.; Casarez, A. D. Org. Lett. 2004, 6, 2161.
17. Wang, K. K.; Nikam, S. S. J. Org. Chem. 1985, 50, 2193.
18. Gaul, C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963.
19. 1 might be subject to eclipsing interactions with the TMS group and that the aldehyde might alternatively approach with the R1 group in a pseudoaxial position. We acknowledge this possibility; however, as the observed diastereoselectivity of the reaction does not fit in with this, it is presumed that the linear nature of the propargyl unit combined with the length of the C-TMS bond causes any interaction to be diminished. Additionally, placing R1 in an axial position might result in deleterious interactions with the bulky borane fragment.