Distinct chemoselectivities in the platinum-catalyzed 1,2- carboalkoxylations of 5-alkoxypent-1-yn-3-ol derivatives

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1702-1705

  Ting, Chun Ming ^a   Wang, Chiou Dong ^a   Chaudhuri, Rupsha ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

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Indexed keywords

EID: 79953208684     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2002144     Document Type: Article

References (26)

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6. For migration of allyl group, see selected examples: Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024
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12. For migration of p -methoxybenzyl (PMB) and other groups, see selected examples: Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546
13. Nakamura, I.; Sato, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 4473
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16. 2-catalyzed cycloisomerization of 2-propargyl anilines gave indole products through a typical 1,2-addition pathway, with no epoxide product 6 in this case. See: Cariou, K.; Ronan, B.; Mignani, S.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2007, 46, 1881
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19. 2 (25 °C, 10 min).
20. For the gem -dialkyl effect of this cyclization, see selected examples: Kostal, J.; Jorgensen, W. L. J. Am. Chem. Soc. 2010, 32, 8766
21. Jager, J.; Graafland, T.; Schenk, H.; Kirby, A. J.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1984, 106, 139
22. Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080
23. X-ray crystallographic data of compound 6o′′ is provided in the Supporting Information.
24. A [3.3]-allyl shift was mentioned in the cycloisomerization of 2-propargyl anilines, but in a distinct mechanism. See ref 4.
25. The detailed procedure for the preparation of enantiomerically enriched alcohol (R)- 5f is provided in the Supporting Information.
26. For the cycloisomerization of compound 5, we exclude a prior 1,3-electrophilic migration as shown by the B → G transformation because we obtained no tractable amount of compound H or H′. Although species G might produce ketone 6a′ alternatively through a 1,2-hydride shift (Pinacol rearrangement), not ketone 6a′ but epoxide 6a is verified to be the primary product in this catalysis.