Simple strategy for synthesis of optically active allylic alcohols and amines by using enantioselective organocatalysis

Proceedings of the National Academy of Sciences of the United States of America

Volumn 107, Issue 48, 2010, Pages 20630-20635

  Jiang, Hao ^a   Holub, Nicole ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Allylic amines; Asymmetric catalysis; Enantioselectivity

Indexed keywords

ALCOHOL DERIVATIVE; AMINE;

CATALYSIS; CHEMICAL STRUCTURE; CONFERENCE PAPER; ENANTIOSELECTIVITY; EPOXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 78650556006     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0914523107     Document Type: Article

References (43)

1. Hoveyda AH, Evans DA, Fu GC (1993) Substrate-directable chemical reactions. Chem Rev 93:1307-1370.
2. Cha JK, Kim N-S (1995) Acyclic stereocontrol induced by allylic alkoxy groups. Synthetic applications of stereoselective dihydroxylation in natural product synthesis. Chem Rev 95:1761-1795.
3. Johansen M, Jørgensen KA (1998) Allylic amination. Chem Rev 98:1689-1708.
4. Gais H-J, Theil F (2002) Enzyme Catalysis in Organic Synthesis, eds K Drauz and H Waldmann (Wiley-VCH, Weinheim), pp 335-578.
5. Johnson RA, Sharpless KB (1993) Catalytic Asymmetric Synthesis, ed I Ojima (Wiley- VCH, New York), pp 103-158.
6. Martin-Matute B, Bäckvall J-E (2008) Dynamic kinetic resolutions. Asymmetric Organic Synthesis with Enzymes (Wiley-VCH, Weinheim, Germany), pp 89-113.
7. Corey EJ, Helal CJ (1998) Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic method. Angew Chem Int Edit 37:1986-2012.
8. Noyori R, Okhuma T (2001) Asymmetric catalysis by architectural and functional molecular engineering: Practical chemo- and stereoselective hydrogenation of ketones. Angew Chem Int Edit 40:40-73.
9. Skucas E, Ngai M-Y, Komanduri V, Krische MJ (2007) Enantiomerically enriched allylic alcohols and allylic amines via C-C bond-forming hydrogenation: Asymmetric carbonyl and imine vinylation. Acc Chem Res 40:1394-1401.
10. Trost BM, Crawley ML (2003) Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis. Chem Rev 103:2921-2944.
11. Lu Z, Ma SM (2008) Metal-catalyzed enantioselective allylation in asymmetric synthesis. Angew Chem Int Edit 47:258-297.
12. Trost BM, Organ MG (1994) Deracemization of cyclic allyl esters. J Am Chem Soc 116:10320-10321.
13. Trost BM, Tsui H-C, Toste FD (2000) Deracemization of Baylis-Hillman adducts. J Am Chem Soc 122:3534-3535.
14. Lüssem BJ, Gais H-J (2003) Palladium-catalyzed deracemization of allylic carbonates in water with formation of allylic alcohols: Hydrogen carbonate ion as nucleophile in the palladium-catalyzed allylic substitution and kinetic resolution. J Am Chem Soc 125:6066-6067.
15. Gais HJ, et al. (2003) Highly selective palladium catalyzed kinetic resolution and enantioselective substitution of racemic allylic carbonates with sulfur nucleophiles: Asymmetric synthesis of allylic sulfides, allylic sulfones, and allylic alcohols. Chem- Eur J 9:4202-4221.
16. Trost BM, Bunt RC (1994) Asymmetric induction in allylic alkylations of 3-(acyloxy)cycloalkenes. J Am Chem Soc 116:4089-4090.
17. Uozumi H, Tanaka K, Shibatomi K (2004) Asymmetric allylic amination in water catalyzed by an amphiphilic resin-supported chiral palladium complex. Org Lett 6:281-283.
18. But TYS, Toy PH (2007) The Mitsunobu reaction: Origin, mechanism, improvements and applications. Chem-Asian J 2:1340-1355.
19. Jiang H, et al. (2009) Target-directed organocatalysis: A direct asymmetric catalytic approach to chiral propargylic and allylic fluorides. J Am Chem Soc 131:7153-7157.
20. Jiao P, Kawasaki M, Yamamoto H (2009) A sequential O-nitrosoaldol and grignard addition process: An enantio- and diastereoselective entry to chiral 1,2-diols. Angew Chem Int Edit 48:3333-3336.
21. Simmons B, Walji AM, MacMillan DWC (2009) Cycle-specific organocascade catalysis: Application to olefin hydroamination, hydro-oxidation, and amino-oxidation, and to natural product synthesis. Angew Chem Int Edit 48:4349-4353.
22. Ishikawa H, Suzuki T, Hayashi Y (2009) High-yielding synthesis of the anti-influenza neuramidase inhibitor (-)-oseltamivir by three "one-pot" operations. Angew Chem Int Edit 48:1304-1307.
23. Enders D, Hüttl MRM, Runsink J, Raabe G, Wendt B (2007) Organocatalytic one-pot asymmetric synthesis of functionalized tricyclic carbon frameworks from a triple-cascade/ diels-alder sequence. Angew Chem Int Edit 46:467-469.
24. Michrowska A, List B (2009) Concise synthesis of ricciocarpin A and discovery of a more potent analogue. Nature Chemistry 1:225-228.
25. Lim SM, Hill N, Myers AG (2009) A method for the preparation of differentiated trans-1,2-diol derivatives with enantio- and diastereocontrol. J Am Chem Soc 131:5763-5765.
26. Melchiorre P, Marigo M, Carlone A, Bartoli G (2008) Asymmetric aminocatalysis-gold rush in organic chemistry. Angew Chem Int Edit 47:6138-6171.
27. MacMillan DWC (2008) The advent and development of organocatalysis. Nature 455:304-308.
28. Dondoni A, Massi A (2008) Asymmetric organocatalysis: From infancy to adolescence. Angew Chem Int Ediy 47:4638-4660.
29. Barbas CF, III (2007) Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus. Angew Chem Int Edit 47:42-47.
30. Erkkila A, Majander I, Pihko PM (2007) Iminium catalysis. Chem Rev 107:5416-5470.
31. Enders D, Grondal C, Hüttl MRM (2007) Asymmetric organocatalytic domino reactions. Angew Chem Int Ediy 46:1570-1581.
32. Wang X-W, Reisinger CM, List B (2008) Catalytic asymmetric epoxidation of cyclic enones. J Am Chem Soc 130:6070-6071.
33. Reisinger CM, Wang X-W, List B (2008) Catalytic asymmetric hydroperoxidation of a,β-unsaturated ketones: An approach to enantiopure peroxyhemiketals, epoxides, and aldols. Angew Chem Int Edit 47:8112-8115.
34. Lu X-J, Liu Y, Sun B-F, Cindric B, Deng Li (2008) Catalytic enantioselective peroxidation of a,β-unsaturated ketones. J Am Chem Soc 130:8134-8135.
35. Pesciaioli F, et al. (2008) Organocatalytic asymmetric aziridination of enones. Angew Chem Int Edit 47:8703-8706.
36. Armstrong S, Baxter CA, Lamont SG, Pape AR, Wincewicz R (2007) Amine-promoted, organocatalytic aziridination of enones. Org Lett 9:351-353.
37. Wharton P, Bohlen DH (1961) Hydrazine reduction of a,β-epoxy ketones to allylic alcohols. J Org Chem 26:3615-3616.
38. Siewert J, Sandmann R, von Zezschwitz P (2007) Rhodium-catalyzed enantioselective 1,2-addition of aluminum organyl compounds to cyclic enones. Angew Chem Int Edit 46:7122-7124.
39. Stork G, Williard PG (1977) Five- and six-membered-ring formation from olefinic a,β-epoxy ketones and hydrazine. J Am Chem Soc 99:7067-7068.
40. Ohloff G, Uhde G (1970) Uncommon cyclization in the reaction of (+)-epoxy-alfa-dihydroionone and hydrazine hydrate. Helv Chim Acta 53:531-541.
41. Stork G, Baine NH (1982) Cyclization of vinyl radicals: A versatile method for the construction of five- and six-membered rings. J Am Chem Soc 104:2321-2323.
42. Carlone A, Marigo M, North C, Landa A, Jørgensen KA (2006) A simple asymmetric organocatalytic approach to optically active cyclohexenones. Chem Commun 47:4928-4930.
43. Skull BK, Sakai T, Nichols JB, Koreeda M (1997) Mitsunobu reaction of unbiased cyclic allylic alcohols. J Org Chem 62:8294-8303.