Stereoselective synthesis of stereotriad subunits of polyketides through additions of nonracemic allenylsilanes to (R)- and (S)-2-methyl-3-oxygenated propanals

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 630-633

  Marshall, James A ^a   Maxson, Karin ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYKETIDE; PROPIONALDEHYDE; SILANE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS; UNITED STATES;

EID: 0034723306     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991543y     Document Type: Article

References (16)

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2. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1999, 64, 5201.
3. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1999, 64, 5201.
4. Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696.
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6. Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870.
7. E2′ pathway. Buckle, M. J. C.; Fleming, I. Tetrahedron Lett. 1993, 34, 2383.
8. Fleming, I.; Terrett, N. K. J. Organomet. Chem. 1984, 264, 99. Fleming, I.; Waterson, D. J. Chem. Soc., Perkin Trans. 1 1984, 1809.
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10. Komatsu, N.; Uda, M.; Suzuki, H.; Takahashi, T.; Domae, T.; Wada, M. Tetrahedron Lett. 1997, 38, 7215.
11. Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745.
12. Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. J. Org. Chem. 1987, 52, 316.
13. This analysis was performed by Dr. Michael Sabat of this department.
14. 3 (matrix presented)
15. Recent work with methylaluminum halide Lewis acids has shown that additions to β-OTBS aldehydes can proceed by chelation-controlled transition states. Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457. Evans, D. A.; Halstead, D. P.; Allison, B. D. Tetrahedron Lett. 1999, 40, 4461.
16. Recent work with methylaluminum halide Lewis acids has shown that additions to β-OTBS aldehydes can proceed by chelation- controlled transition states. Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457. Evans, D. A.; Halstead, D. P.; Allison, B. D. Tetrahedron Lett. 1999, 40, 4461.