Heterobimetallic Catalysis in Asymmetric 1,4-Addition of O-Alkylhydroxylamine to Enones

Journal of the American Chemical Society

Volumn 125, Issue 52, 2003, Pages 16178-16179

  Yamagiwa, Noriyuki ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HYDROXYLAMINE; KETONE; LITHIUM; ORGANOMETALLIC COMPOUND; YTTERBIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL SYMPATHECTOMY; CHEMISTRY; CHIRALITY; ENANTIOSELECTIVITY; VOLUMETRY;

ALKENES; CATALYSIS; HYDROXYLAMINES; KETONES; LITHIUM; ORGANOMETALLIC COMPOUNDS; YTTERBIUM;

EID: 0347694999     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038688d     Document Type: Article

References (24)

1. Reviews for enantioselective conjugate addition: (a) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
2. (b) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
3. 3 ion: (a) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959.
4. (b) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134.
5. Aromatic amine: (c) Zhuang, W.; Hazell, R. G.; Jørgensen, K. A. Chem. Commun. 2001, 1240.
6. Lithium amide: (d) Doi, H.; Sakai, T.; Iguchi, M.; Yamada, K.; Tomioka, K. J. Am. Chem. Soc. 2003, 125, 2886 and references therein.
7. For other methods for the preparation of β-amino carbonyl segments, see reviews: (e) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
8. (f) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
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11. (b) Jørgensen, K. A.; Falborg, L. J. Chem. Soc., Perkin Trans. 1 1996, 2823.
12. (c) Sugihara, H.; Daikai, K.; Jin, X. L.; Furuno, H.; Inanaga, J. Tetrahedron Lett. 2002, 43, 2735.
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14. (e) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Kim, H.; Perciaccante, R.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 2395.
15. During preparation of this manuscript, Sibi reported excellent results with N-benzylhydroxylamine as nucleophile using 5 mol % catalyst. (a) Sibi, M. P.; Prabagaran, N.; Ghorpade, S. G.; Jasperse, C. P. J. Am. Chem. Soc. 2003, 125, 11796 and references therein.
16. With N-benzylhydroxylamine as a nucleophile, conversion of the 1, 4-adduct into aziridine was not reported. For difference in properties of O-alkylhydroxylamine and N-alkylhydroxylamine, see: (b) Niu, D.; Zhao, K. J. Am. Chem. Soc. 1999, 121, 2456.
17. (c) Sibi, M. P.; Liu, M. Org. Lett. 2000, 2, 3393.
18. Review: (a) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
19. (b) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236.
20. For the preparation and structure of YLB 1a, see: (c) Aspinall, H. C.; Dwyer, J. L.; Greeves, N.; Steiner, A. Organometallics 1999, 18, 1366.
21. (a) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636.
22. (b) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2003, 5, 3021.
23. Inanaga achieved excellent ee (94-99% ee, ref 3d) using O-diphenylmethylhydroxylamine, which is not commercially available.
24. See the Supporting Information for the detailed results.