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33745667603
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note
-
2 gave only allenyl aldehyde 2 even the presence of water. THF and dioxane afforded the desired pyran in 14 and 4 h, respectively. Reactions in DME returned only starting material.
-
-
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45
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33745659060
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note
-
8aan unidentified aldehyde.
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-
-
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46
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33745654615
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note
-
Relative stereochemistry was ascertained through nOe analysis; see Supporting Information for details.
-
-
-
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47
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33745672604
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note
-
The enantiomeric excess of pyran 6f was determined after in situ reduction to the corresponding allylic alcohol (see Supporting Information for details).
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50
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0001495226
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Apsimon, J., Ed.; Wiley: New York
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An alternative mechanism in which gold(I) catalyzes the addition of the hemiacetal, not the aldehyde, to the allene is also possible. See: (a) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
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