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During the preparation of this manuscript, the Au(I)-catalyzed cyclization of alkynyl tert-butyl carbonates has been reported: (a) Buzas, A.; Gagosz, F. Org. Lett. 2006, 3, 515-518.
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33745451902
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note
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Substrate 1 was prepared in 91% yield by the reaction of N-Boc-p-anisidine with propargyl bromide. See Supporting Information for details.
-
-
-
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48
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33244465401
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3Cl and silver salts, see for instance: ref 8b,c,e,f. See also: Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798-1799.
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49
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33745456229
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-
note
-
6 alone as catalyst provided the cyclization product 2 but with only 73% of conversion after 24 h.
-
-
-
-
50
-
-
33745435454
-
-
note
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The stereochemistry was assigned in the case of oxazolidinone 6 by a NOESY experiment (a strong cross-peak was observed between the olefinic proton and the allylic protons).
-
-
-
-
51
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33745452406
-
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note
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For gold-catalyzed addition of alcohols to alkynes, see ref 10b,c.
-
-
-
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52
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33745477679
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note
-
2 (2 h) afforded a 35:65 mixture of the oxazolidinone 26 and its tert-butyl ether. These compounds were isolated in 28 and 59% yields after silica gel chromatography. (Diagram presented).
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53
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0035914638
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These substrates were prepared by a reaction of 3-butynyl-1- methanesulfonate with the corresponding amine and further BOC protection. See: Fürstner, A.; Guth, O.; Düffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem.-Eur. J. 2001, 7, 4811-4820.
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20844431887
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For other processes with the N-Boc group acting as nucleophile in cyclization reactions, see for instance: (a) Hanessian, S.; Tremblay, M.; Marzi, M.; Del Valle, J. R. J. Org. Chem. 2005, 70, 5070-5085.
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33745463719
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note
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2 at room temperature, cyclic products were not detected at all and only partial or complete N-Boc deprotection was observed.
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