Regioselectivity in the palladium-catalyzed addition of carbon nucleophiles to dihydropyran derivatives

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1257-1263

  Brescia, Marc Raleigh ^a   Shimshock, Yvonne Class ^a   DeShong, Philip ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAN DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030891739     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961973d     Document Type: Article

References (24)

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2. (b) For a discussion of the regioselectivity of Pd-catalyzed alkylation in allylic systems with a heteroatom directly attached to the allyl system, see: Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Permagon Press: New York, 1991; Vol. 4, pp 615-635, and references cited therein.
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8. Pseudomonic acid numbering. We shall use pyran numbering throughout the remainder of the manuscript.
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12. It was recognized that the relative stereochemistry of the two substituents on dihydropyran 2 would also play a role in controlling the regiochemistry of nucleophilic attack; however, we anticipated that the general features of the addition would not be altered by the relative stereochemistry of the substituents. See also: Curran, D. P.; Suh, Y. G. Carbohydrate Res. 1987, 171, 161-191.
13. A standard protocol for the alkylation was employed for these studies in an effort to minimize concerns about the regioselectivity arising from differences in the reaction conditions or catalysts involved. In some instances, the yields of adduct suffered from lack of optimization of reaction conditions.
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17. 2-complexes in alkylation reactions has been discussed by several authors. See: (a) Trost, B. M.; Verhoeven, T. R. J. Org. Chem. 1976, 41, 3215-3216. (b) Fiaud, J. C.; Malleron, J. L. Tetrahedron Lett. 1981, 22, 1399-1402. (c) Akermark, B.; Hansson, S.; Krakenberger, B.; Vitagliano, A.; Zetterberg, K. Organometallics 1984, 3, 679-682. (d) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem 1990, 55, 3019-3023.
18. 2-complexes in alkylation reactions has been discussed by several authors. See: (a) Trost, B. M.; Verhoeven, T. R. J. Org. Chem. 1976, 41, 3215-3216. (b) Fiaud, J. C.; Malleron, J. L. Tetrahedron Lett. 1981, 22, 1399-1402. (c) Akermark, B.; Hansson, S.; Krakenberger, B.; Vitagliano, A.; Zetterberg, K. Organometallics 1984, 3, 679-682. (d) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem 1990, 55, 3019-3023.
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