Copper-catalyzed enantioselective propargylic amination of nonaromatic propargylic esters with amines

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2460-2463

  Yoshida, Akiko ^a   Hattori, Gaku ^a   Miyake, Yoshihiro ^a   Nishibayashi, Yoshiaki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955619524     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200703g     Document Type: Article

References (47)

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6. The copper-catalyzed enantioselective propargylic alkylation of propargylic acetates with enamines was reported by using our reaction system, where Cl-MeO-BIPHEP and BINAP worked as good chiral ligands; see: Fang, P.; Hou, X.-L. Org. Lett. 2009, 11, 4612
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11. Prof. van Maarseveen and co-workers achieved the first enantioselective propargylic amination and presented a part of their result at the PAC-Symposium 2007, (March 1, 2007, Utrecht).
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28. Prof. van Maarseveen and co-workers have already found the copper-catalyzed enantioselective propargylic amination of propargylic acetates bearing an alkyl group at the propargylic position by using pybox derivatives as a chiral ligands. However, the detailed result has been reported only in a Ph.D. thesis; see: Detz, R. J., Ph.D. thesis, University of Amsterdam (2009).
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36. BIPHEP = 2,2′-Bis(diphenylphosphino)-1,1′-biphenyl.
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45. Separately, we confirmed that no effective kinetic resolution occurred effectively under these reaction conditions. In fact, the catalytic reaction of 1a with N -methylaniline was carried out only for 24 h; 1a was recovered in 16% recovery with 32% ee together with 2a in 31% yield with 84% ee.
46. The reaction of 1-cyclohexyl-3-phenyl-1-propynyl pentafluorobenzoate with N -methylaniline under the same reaction conditions gave the corresponding propargylic alcohol in 92% NMR yield. This result indicates that only the use of propargylic esters bearing a terminal alkyne moiety were available as substrates.
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