Direct asymmetric iodination of aldehydes using an axially chiral bifunctional amino alcohol catalyst

Journal of the American Chemical Society

Volumn 130, Issue 12, 2008, Pages 3728-3729

  Kano, Taichi ^a   Ueda, Mitsuhiro ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AMINOALCOHOL;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HALOGENATION; IODINATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ALDEHYDES; AMINO ALCOHOLS; CATALYSIS; HALOGENATION; HYDROGEN BONDING; MOLECULAR STRUCTURE; STEREOISOMERISM; SUCCINIMIDES;

EID: 41149147540     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074003o     Document Type: Article

References (17)

1. For reviews, see: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
2. (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
3. (c) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH: Weinheim, 2005.
4. (d) Enantioselective Organocatalysis; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, 2007.
5. For reviews, see: Marigo, M.; Jørgensen, K. A. Chem. Commun. 2006, 2001.
6. For instance, an optically active α-iodoaldehyde in ether is partially racemized by a catalytic amount of pyrrolidine at 0°C, while almost no racemization occurs under similar conditions in the absence of pyrrolidine; see Supporting Information for detail.
7. Fluorination: (a) Enders, D.; Hüttl, M. R. M. Synlett 2005, 991.
8. (b) Marigo, M.; Fielenbach, D.; Braunton, A.; Kjœrsgaard, A.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 3703.
9. (c) Steiner, D. D.; Mase, N.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2005, 44, 3706.
10. (d) Beeson, T. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 8826.
11. Chlorination: (a) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108.
12. (b) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790.
13. Bromination and Iodination: Bertelsen, S.; Halland, N.; Bachmann, S.; Marigo, M.; Braunton, A.; Jørgensen, K. A. Chem. Commun. 2005, 4821.
14. Asymmetric synthesis of α-iodoaldehydes using a chiral auxiliary: Jacoby, C.; Braekman, J.-C.; Daloze, D. Tetrahedron 1996, 52, 10473.
15. Kano, T.; Ueda, M.; Takai, J.; Maruoka, K. J. Am. Chem. Soc. 2006, 128, 6046.
16. Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett. 2002, 43, 9703.
17. Under similar conditions the corresponding α-chloroaldehyde was silyl-cyanated with low diastereoselectivity (9% de).