Copper-catalyzed intramolecular hydroamination of allenylamines to 3-pyrrolines or 2-alkenylpyrrolidines

Tetrahedron Letters

Volumn 49, Issue 46, 2008, Pages 6529-6532

  Tsuhako, Akiko ^a   Oikawa, Daisuke ^a   Sakai, Kazushi ^a   Okamoto, Sentaro ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; COPPER; COPPER CHLORIDE; CUPRIC CHLORIDE; PYRROLIDINE DERIVATIVE; PYRROLINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; INTAMOLECULAR HYDROAMINATION; STEREOSPECIFICITY;

EID: 52949124402     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.003     Document Type: Article

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54. 3) δ: 2b, 7.10-7.95 (m, 10H), 5.85 (d, J = 4.5 Hz, 1H), 5.72 (d, J = 4.5 Hz, 1H), 4.61 (br s, 1H), 3.97 (d, J = 13.5 Hz, 1H), 3.75 (dd, J = 4.5, 14.0 Hz, 1H), 3.55 (d, J = 13.5 Hz, 1H), 3.31 (dd, J = 5.5, 14.0 Hz, 1H); 2h 6.90-7.50 (m, 15H), (for anit, dl) 5.97 (br s, 1H), 4.98 (br s, 1H), 3.73 (d, J = 14.5 Hz, 1H), 3.25 (d, J = 14.5 Hz, 1H), (for syn, meso) 5.68 (br s, 1H), 4.85 (br s, 1H), 3.82 (s, 2H); 2i 7.10-7.50 (m, 10H), 1.10-1.70 (m, 10H), 0.88 (t, J = .2 Hz, 3H), (for major) 5.72 (br d, J = 6.0 Hz, 1H), 5.58 (br d, J = 5.4 Hz, 1H), 4.68 (dt, J = 4.8, 2.4 Hz, 1H), 3.92 (d, J = 13.8 Hz, 1H), 3.82 (m, 1H), 3.80 (d, J = 13.8 Hz, 1H), (for minor), 5.97 (br d, J = 6.6 Hz, 1H), 5.81 (br s, J = 6.0 Hz, 1H), 4.79 (d, J = 5.4 Hz, 1H), 3.69 (m, 1H), 3.81 (d, J = 14.4 Hz, 1H), 3.49 (d, J = 14.4 Hz, 1H); 2j, 6.90-7.40 (m, 10H), 5.73 (br s, 1H), 5.52 (br s, 1H), 4.80 (br s, 1H), 3.91 (t, J = 5.5 Hz, 1H), 3.61-3.83 (m, 3 H), 3.58 (dd, J = 6.8, 9.6 Hz, 1H), 3.15 (s, 3H); 2k, 7.10-7.45 (m, 15H), 6.31 (dd, J = 2.5, 4.0 Hz, 1H), 5.04 (br s, 1H), 3.83 (d, J = 13.0 Hz, 1H), 3.82 (ddd, J = 1.5, 5.5, 14.0 Hz, 1H), 3.62 (d, J = 13.0 Hz, 1H), 3.55 (ddd, J = 1.5, 4.0, 14.0 Hz, 1H); 2l, 7.41 (d, J = 8.0 Hz, 2H), 7.25 (d, J = 8.0 Hz, 2H), 5.80 (d, J = 3.5 Hz, 1H), 5.56 (d, J = 3.5 Hz, 1H), 4.66 (br s, 1H), 3.84 (dd, J = 5.5, 14.5 Hz, 1H), 3.57 (dt, J = 14.5, 3.0 Hz, 1H), 2.86 (hept, J = 6.0 Hz, 1H), 0.99 (d, J = 6.5 Hz, 3H), 0.96 (d, J = 6.0 Hz, 3H); 3f, 7.04-7.42 (m, 10H), 5.86 (ddd, J = 6.9, 10.3, 17.2 Hz, 1H), 5.12 (d, J = 17.2 Hz, 1H), 4.97 (d, J = 10.3 Hz, 1H), 3.76 (d, J = 10.9 Hz, 1H), 3.74 (m, 1H), 3.45 (d, J = 10.9 Hz, 1H), 2.75 (ddd, J = 1.7, 6.9, 12.6 Hz, 1H), 2.25 (dd, J = 9.2, 12.6 Hz, 1H); 3g, 7.18-7.34 (m, 5H), 5.61 (dt, J = 14.9, 6.9 Hz, 1H), 5.38 (dd, J = 8.0, 14.5 Hz, 1H), 4.04 (d, J = 13.2 Hz, 1H), 3.02 (d, J = 13.2 Hz, 1H), 2.92 (t, J = 8.1 Hz, 1H), 2.72 (q, J = 8.0 Hz, 1H), 2.02-2.10 (m, 3H), 1.93 (m, 1H), 1.57-1.80 (m, 3H), 1.36-1.47 (m, 2H), 0.91 (t, J = 7.5 Hz, 3H).
55. 2 complexes with propargyl compounds. See: Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. For synthesis of 1g, see Ref. 2b.
56. 2 (10 mol %) as a proton scavenger could rule out the possibility of the role of a proton as an actual catalyst.