Controlled one-pot sequence of three Ad(E) reactions as a novel protocol for the synthesis of polyfunctional compounds

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1083-1086

  Lazareva, Margarita I ^a,b   Kryschenko, Yury K ^a,c   Hayford, Anthony ^a   Lovdahl, Mark ^a   Caple, Ron ^a   Smit, William A ^b,d  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^c RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

^d MACALESTER COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; POLYFUNCTIONAL GROUP; REAGENT; SULFONIUM DERIVATIVE;

ARTICLE; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032485224     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10785-7     Document Type: Article

References (12)

1. 1. For the pertinent data see a review, Smit, W. A.; Caple, R.; Smoliakova, I. P. Chem. Rev., 1994, 94, 2359-2382.
2. 2. Smoliakova, I. P.; Caple, R.; Magnuson, V. R.; Polyakov, V. R.; Smit, W. A.; Shashkov, A. S.; Ohinov, B. D. J. Chem. Soc. Perkin Trans. 1, 1995, 1065-1069; see also references cited therein.
3. 3. Intermediate 2 was formed nearly quantitatively as estimated by 92% isolated yield of 3-methoxy-4-p-tolylthiobutanal upon the quenching of the reaction mixture with water.
4. 4 as a catalyst in the reactions involving intermediacy of carbocationic species, see for example: Mukaiyama aldol addition, Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox D. N. A. Tetrahedron, 1992, 48, 5731-5742; Reetz, M. T.; Fox D. N. A. Tetrahedron Lett., 1993, 34, 1119-1122; addition of allylstannanes to aldehydes, Henry, K. J., Jr.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett., 1992, 33, 1617-1620; 1,2-methyl shifts in ESI-like intermediates, Borisov, A. B.; Bodrikov, I. V.; Borisova, G. N.; Bel'sky, V. K.; Smit, W. A.; Lutsenko, A. I. J. Chem. Soc. Mendeleev Commun., 1996, 52-53.
5. 4 as a catalyst in the reactions involving intermediacy of carbocationic species, see for example: Mukaiyama aldol addition, Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox D. N. A. Tetrahedron, 1992, 48, 5731-5742; Reetz, M. T.; Fox D. N. A. Tetrahedron Lett., 1993, 34, 1119-1122; addition of allylstannanes to aldehydes, Henry, K. J., Jr.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett., 1992, 33, 1617-1620; 1,2-methyl shifts in ESI-like intermediates, Borisov, A. B.; Bodrikov, I. V.; Borisova, G. N.; Bel'sky, V. K.; Smit, W. A.; Lutsenko, A. I. J. Chem. Soc. Mendeleev Commun., 1996, 52-53.
6. 4 as a catalyst in the reactions involving intermediacy of carbocationic species, see for example: Mukaiyama aldol addition, Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox D. N. A. Tetrahedron, 1992, 48, 5731-5742; Reetz, M. T.; Fox D. N. A. Tetrahedron Lett., 1993, 34, 1119-1122; addition of allylstannanes to aldehydes, Henry, K. J., Jr.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett., 1992, 33, 1617-1620; 1,2-methyl shifts in ESI-like intermediates, Borisov, A. B.; Bodrikov, I. V.; Borisova, G. N.; Bel'sky, V. K.; Smit, W. A.; Lutsenko, A. I. J. Chem. Soc. Mendeleev Commun., 1996, 52-53.
7. 4 as a catalyst in the reactions involving intermediacy of carbocationic species, see for example: Mukaiyama aldol addition, Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox D. N. A. Tetrahedron, 1992, 48, 5731-5742; Reetz, M. T.; Fox D. N. A. Tetrahedron Lett., 1993, 34, 1119-1122; addition of allylstannanes to aldehydes, Henry, K. J., Jr.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett., 1992, 33, 1617-1620; 1,2-methyl shifts in ESI-like intermediates, Borisov, A. B.; Bodrikov, I. V.; Borisova, G. N.; Bel'sky, V. K.; Smit, W. A.; Lutsenko, A. I. J. Chem. Soc. Mendeleev Commun., 1996, 52-53.
8. 5. Yamamoto, Y.; Asao, N. Chem. Rev., 1993, 2207-2293.
9. 2=), 5.78 (m, 1H, CH=), 7.07 and 7.27 (2d, 4H-arom, J=8.0 Hz) ppm.
10. 7. Perlmuter, P. Conjugated Addition Reactions in Organic Synthesis, Tetrahedron Organic Series; Pergamon: Oxford, 1992.
11. 8. Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press, Inc: Boca Raton, 1996.
12. 2).