Silyloxy-cope rearrangement of chiral aldol adducts

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4471-4474

  Black, W Cameron ^a   Giroux, André ^a   Greidanus, Grace ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ORGANIC COMPOUND; SILANE DERIVATIVE; XYLENE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; MOLECULAR MODEL; POLYMERIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TEMPERATURE MEASUREMENT;

EID: 0030600169     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00904-5     Document Type: Article

References (9)

1. 1. (a) Nicolas, E.; Russell, K.C.; Hruby, V.J. J. Org. Chem. 1993, 58, 766-770.
2. (b) Williams, D.R.; Li, J. Tetrahedron Lett. 1994, 5113-5116.
3. 2. Evans, D.A.; Chapman, K.T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
4. 3. Evans, DA.; Sjogren, E.B.; Bartroli, J.; Dow, R.L. Tetrahedron Lett. 1986, 4957-60.
5. 3) δ 7.4 - 7.1 (m, 10H), 6.29 (dd, J = 5.8, 0.8 Hz, 1H), 6.24 (m, 1H), 5.85 (m, 1H), 4.72 (m, 1H), 4.63 (dd, J = 9.8, 5.6 Hz, 1H), 4.34 (dd, J = 8.9, 8.3 Hz, 1H), 4.22 (dd, J = 8.9, 3.2 Hz, 1H), 3.96 (m, 1H), 3.64 (dd, J = 4.6, 3.4 Hz, 1H), 3.31 (m, 1H), 3.09 (dd, J = 13.4, 3.2 Hz, 1H), 2.85 (dd, J = 13.4, 8.7 Hz, 1H), 2.71 (m, 1H), 2.12 (m, 1H), 1.83 (m, 2H), 1.66 (m, 1H), 1.40 (m, 1H), 0.95 (s, 9H), 0.17 (s, 3H), 0.11 (s, 3H).
6. 5. (a) Hill, R. K.; Gilman, N. W. J. Chem . Soc., Chem. Comm. 1967, 619-620.
7. (b) Doering, W. v. E.; Roth, W. R. Tetrahedron 1962, 18, 67-74.
8. 6. Bettoni, G.; Cellucci, C.; Tortorella, V. J. Heterocyclic Chem. 1976, 13, 1053-55.
9. 7. 3-Phenoxypropenal and 3-thiophenylpropenal were prepared by phenol or thiophenol addition to propynal in the presence of triethylamine. Alternatively, 3-thiophenylpropenal could be prepared using literature methods (Danda, H.; Hansen, M. M.; Heathcock, C. H. J. Org. Chem. 1990, 55, 173-181). The aldol reactions of these heteroatom-substituted aldehydes provided mixed results. With the thiophenyl-and phenol-substituted aldehydes, the aldol reactions (unoptimized) proceeded in 75% and 46% yield respectively, while attempts at the aldol reaction using or ethoxy-or N-methylaniline-substituted aldehydes were unsuccessful.