Enantioselective iron-catalysed O-H bond insertions

Nature Chemistry

Volumn 2, Issue 7, 2010, Pages 546-551

  Zhu, Shou Fei ^a   Cai, Yan ^a   Mao, Hong Xiang ^a   Xie, Jian Hua ^a   Zhou, Qi Lin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IRON; OXYGEN; TRANSITION ELEMENT; WATER;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; IRON; OXYGEN; STEREOISOMERISM; TRANSITION ELEMENTS; WATER;

EID: 77954009559     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.651     Document Type: Article

References (32)

1. Jacobson, E. N., Pfaltz, A. & Yamamoto, H. (eds) Comprehensive Asymmetric Catalysis and supplement 1 and 2 (Springer, 1999, 2004).
2. Yoon, T. P. & Jacobsen, E. N. Privileged chiral catalysts. Science 299, 1691-1693 (2003).
3. Bolm, C. A new iron age. Nature Chem. 1, 420 (2009).
4. Plietker, B. (ed.) Iron Catalysis in Organic Chemistry (Wiley-VCH, 2008).
5. Bolm, C., Legros, J., Le Paih, J. & Zani, L. Iron-catalyzed reaction in organic synthesis. Chem. Rev. 104, 6217-6254 (2004).
6. Enthaler, S., Junge, K. & Beller, M. Sustainable metal catalysis with iron: from rust to a rising star? Angew. Chem. Int. Ed. 47, 3317-3321 (2008).
7. Sherry, B. D. & Fürstner, A. The promise and challenge of iron-catalyzed cross coupling. Acc. Chem. Res. 41, 1500-1511 (2008).
8. Corey, E. J., Imai, N. & Zhang, H.-Y. Designed catalyst for enantioselective Diels-Alder addition from a C2-symmetric chiral bis(oxazoline)-Fe(III) complex. J. Am. Chem. Soc. 113, 728-729 (1991).
9. Suzuki, K., Oldenburg, P. D. & Que, L. Jr. Iron-catalyzed asymmetric olefin cis-dihydoxylation with 97% enantiomeric excess. Angew. Chem. Int. Ed. 47, 1887-1889 (2008).
10. Shaikh, N. S., Enthaler, S., Junge, K. & Beller, M. Iron-catalyzed enantioselective hydrosilylation of ketones. Angew. Chem. Int. Ed. 47, 2497-2501 (2008).
11. Langlotz, B. K.,Wadepohl, H. & Gade, L. H. Chiral bis(pyridylimino)isoindoles: a highly modular class of pincer ligands for enantioselective catalysis. Angew. Chem. Int. Ed. 47, 4670-4674 (2008).
12. Mikhailine, A., Lough, A. J. & Morris, R. H. Efficient asymmetric transfer hydrogenation of ketones catalyzed by an iron complex containing a P-N-N-P tetradentate ligand formed by template synthesis. J. Am. Chem. Soc. 131, 1394-1395 (2009).
13. Egami, H. & Katsuki, T. Iron-catalyzed asymmetric aerobic oxidation: oxidative coupling of 2-naphthols. J. Am. Chem. Soc. 131, 6082-6083 (2009).
14. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals 4th edn, vol.11 (Wiley-Interscience, 2005).
15. Doyle, M. P., McKervey, M. A. & Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds (Wiley, 1998).
16. Davies, H. M. L. & Manning, J. R. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion. Nature 451, 417-424 (2008).
17. Ge, M. & Corey, E. J. A method for the catalytic enantioselective synthesis of 6-silylated 2-cyclohexenones. Tetrahedron Lett. 47, 2319-2321 (2006). (Pubitemid 43361665)
18. Maier, T. C. & Fu, G. C. Catalytic enantioselective O-H insertion reaction. J. Am. Chem. Soc. 128, 4594-4595 (2006).
19. Liu, B., Zhu, S.-F., Zhang, W., Chen, C. & Zhou, Q.-L. Highly enantioselective insertion of carbenoids into N-H bonds catalyzed by copper complexes of chiral bisoxazolines. J. Am. Chem. Soc. 129, 5834-5835 (2007). (Pubitemid 46748484)
20. Lee, E. C. & Fu, G. C. Copper-catalyzed asymmeric N-H insertion reactions: coupling of diazo compounds with carbamates to generate a-amino acids. J. Am. Chem. Soc. 129, 12066-12067 (2007).
21. Chen, C., Zhu, S.-F., Liu, B., Wang, L.-X. & Zhou, Q.-L. Highly enantioselective insertion of carbenoids into O-H bonds of phenols: an efficient approach to chiral a-aryloxycarboxylic esters. J. Am. Chem. Soc. 129, 12616-12617 (2007).
22. Zhu, S.-F., Chen, C., Cai, Y. & Zhou, Q.-L. Catalytic asymmetric reaction with water: enantioselective synthesis of a-hydroxyesters by a copper-carbenoid O-H insertion reaction. Angew. Chem. Int. Ed. 47, 932-934 (2008).
23. Jolly, P.W. & Pettit, R. Evidence for a novel metal-carbene system. J. Am. Chem. Soc. 88, 5044-5045 (1966).
24. Redlich, M. & Hossain, M. M. Synthesis of asymmetric iron-pybox complexes and their application to aziridine forming reaction. Tetrahedron Lett. 45, 8987-8990 (2004).
25. Liu, B., Zhu, S.-F., Wang, L.-X. & Zhou, Q.-L. Preparation and application of bisoxazoline ligands with a chiral spirobiindane skeleton for asymmetric cyclopropanation and allylic oxidation. Tetrahedron Asymm. 17, 634-641 (2006).
26. Schmidt, B. & Wildemann, H. Diastereoselective ring-closing metathesis in the synthesis of dihydropyrans. J. Org. Chem. 65, 5817-5822 (2000).
27. Schmidt, B. Ruthenium-catalyzed olefin metathesis double-bond isomerization sequence. J. Org. Chem. 69, 7672-7687 (2004).
28. De Benassuti, L., Garanti, L. & Molteni, G. Stereoselective intramolecular cycloaddition of homochiral nitrilimines: synthesis of enantiopure (6S)- substituted-2,3,3a,4,5,6-hexahydrofuro[3,4-c]pyrazoles. Tetrahedron Asymm. 15, 1127-1131 (2004).
29. Cierpucha, M., Solecka, J., Frelek, J., Szczukiewicz, P. & Chmielewski, M. Synthesis, biological and chiroptical active of 3-phenyl-clavams. Bioorg. Med. Chem. 12, 405-416 (2004).
30. Schmidt, B. & Nave, S. Palladium-catalyzed O-allylation of a-hydroxy carbonyl compounds. Adv. Synth. Catal. 348, 531-537 (2006) and therein.
31. Grimley, J. Pharma challenged: market shifts and generic competition create dynamic environment for drug developers. Chem. Eng. News 84, 17 (2006).
32. Castaldi, G., Barreca, G. & Bologna, A. A process for the preparation of clopidogrel. WO 03093276 (2003).