Palladium-catalyzed regio- and stereoselective synthesis of N-protected 2,4-dialkylated azacyclobutanes from amino allenes

Tetrahedron Letters

Volumn 40, Issue 41, 1999, Pages 7393-7397

  Anzai, Miyuki ^a   Toda, Ayako ^a   Ohno, Hiroaki ^a   Takemoto, Yoshiji ^a   Fujii, Nobutaka ^a   Ibuka, Toshiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; AZETIDINE DERIVATIVE; CARBONIC ACID DERIVATIVE; IODIDE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033536722     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01517-8     Document Type: Article

References (37)

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29. 8. For a report of the azetidination of an amino allene, see: Kang, S.-K.; Baik, T.-G.; Kulak, A. N. Synlett 1999, 324. See also: Kang, S.-K.; Baik, T.-G.; Hur, Y. Tetrahedron 1999, 55, 6863. Palladium-catalyzed cyclizations of β-amino allenes yielding azetidines have been independently found by Rutjes, Hiemstra, and co-workers, see: Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. in press.
30. 8. For a report of the azetidination of an amino allene, see: Kang, S.-K.; Baik, T.-G.; Kulak, A. N. Synlett 1999, 324. See also: Kang, S.-K.; Baik, T.-G.; Hur, Y. Tetrahedron 1999, 55, 6863. Palladium-catalyzed cyclizations of β-amino allenes yielding azetidines have been independently found by Rutjes, Hiemstra, and co-workers, see: Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. in press.
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37. 13. Transition metal-assisted cyclization of amino allenes affording six-membered azacycles has been extensively studied. In fact, silver(I)-catalyzed cyclization reaction of amino allene 21 leads exclusively to the six-membered azacycle 22 in 92% isolated yield. Details will be reported in a full paper. (formula presented)