Molybdenum-catalyzed and tungsten-catalyzed enantioselective allylic substitutions

Topics in Organometallic Chemistry

Volumn 38, Issue , 2012, Pages 209-234

  Moberg, Christina ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Allylation; Bispyridylamide; Molybdenum; Phosphinooxazoline; Regioselectivity; Tungsten

Indexed keywords

EID: 82055194065     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418_2011_11     Document Type: Article

References (57)

1. Trost BM, Lautens M (1982) Molybdenum catalysts for allylic alkylation. J Am Chem Soc 104:5543
2. Trost BM, Hung M-H (1983) Tungsten-catalyzed allylic alkylations. New avenues for selectivity. J Am Chem Soc 105:7757
3. Belda O, Moberg C (2004) Molybdenum-catalyzed asymmetric allylic alkylations. Acc Chem Res 37:159
4. Pfaltz A, Lautens M (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis. Springer, Berlin, p 833
5. Trost BM, Crawley ML (2003) Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis. Chem Rev 103:2921
6. Lu Z, Ma S (2008) Metal-catalyzed enantioselective allylation in asymmetric synthesis. Angew Chem Int Ed 47:258
7. Trost BM, Tometzki GB, Hung M-H (1987) Unusual chemoselectivity using difunctional allylic alkylating agents. J Am Chem Soc 109:2176
8. Kubas GJ, Van Der Sluys LS (1990) Tricarbonyltris(nitrile) complexes of Cr, Mo, and W. Inorg Synth 28:29
9. Cotton FA, McCleverty JA, White JE (1990) Tricarbonyl(cycloheptatriene) molybdenum(0). Inorg Synth 28:45
10. Kubas GJ (1983) Preparation and use of W(CO)3(NCR)3 (R = Et, Pr) as improved starting materials for synthesis of tricarbonyl(Z6-cycloheptatriene) tungsten and other substituted carbonyl complexes. Inorg Chem 22:692
11. Kaiser N-FK, Bremberg U, Larhed M, Moberg C, Hallberg A (2000) Fast, convenient, and efficient molybdenum-catalyzed asymmetric allylic alkylation under noninert conditions: An example of microwave promoted fast chemistry. Angew Chem Int Ed 39:3596
12. Trost BM, Lautens M, Hung M-H, Carmichael CS (1984) Tandem alkylation-cycloadditions. Control by transition-metal templates. J Am Chem Soc 106:7641
13. Palucki M, Um JM, Conlon DA, Yasuda N, Hughes DL, Mao B, Wang J, Reider PJ (2001) Molybdenum-catalyzed asymmetric allylic alkylation reactions using Mo(CO)6 as precatalyst. Adv Synth Catal 343:46
14. Lehmann J, Lloyd-Jones GC (1995) Regiocontrol and stereoselectivity in tungsten-bipyridine catalysed allylic alkylation. Tetrahedron 51:8863
15. Trost BM, Hung M-H (1984) On the regiochemistry of metal-catalyzed allylic alkylation: A model. J Am Chem Soc 106:6837
16. Frisell H, A ̊ kermark B (1995) Influence of different 4,7-substituted 1,10-phenanthroline ligands on reactivity and regio- and stereocontrol in tungsten-catalyzed allylic alkylations. Organometallics 14:561
17. Trost BM, Zhang Y (2007) Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles. J Am Chem Soc 129:14548
18. Trost BM, Zhang Y (2010) Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles. Chem Eur J 16:296
19. Trost BM, Lautens M (1987) Chemoselectivity and stereocontrol in molybdenum-catalyzed allylic alkylations. J Am Chem Soc 109:1469
20. Trost BM, Lautens M (1983) Regiochemical control in the molybdenum-catalyzed reactions of trimethylsilyl- and ester-substituted allylic acetates. Organometallics 2:1687
21. Faller JW, Linebarrier D (1988) Reversal of stereochemical path in allylic alkylations promoted by palladium and molybdenum complexes. Organometallics 7:1670
22. Lloyd-Jones GC, Krska SW, Hughes DL, Gouriou L, Bonnet VD, Jack K, Sun Y, Reamer RA (2004) Conclusive evidence for a retention-retention pathway for the molybdenum-catalyzed asymmetric alkylation. J Am Chem Soc 126:702
23. Lloyd-Jones GC, Muños MP (2007) Isotopic labelling in the study of organic and organometallic mechanism and structure: An account. J Label Cmpd Radiopharm 50:1072
24. Malkov AV, Gouriou L, Lloyd-Jones GC, Starý I, Langer V, Spoor P, Vinader V, Koĉovský P (2006) Asymmetric allylic substitution catalyzed by C1-symmetrical complexes of molybdenum: Structural requirements of the ligand and the stereochemical course of the reaction. Chem Eur J 12:6910
25. Trost BM (2002) Pd asymmetric allylic alkylation (AAA). A powerful synthetic tool. Chem Pharm Bull 50:1
26. Hughes DL, Palucki M, Yasuda N, Reamer RA, Reider PJ (2002) Solvent-dependent dynamic kinetic asymmetric transformation/kinetic resolution in molybdenum-catalyzed asymmetric allylic alkylations. J Org Chem 67:2762
27. Lloyd-Jones GC, Pfaltz A (1995) Chiral phosphanodihydrooxazoles in asymmetric catalysis: Tungsten-catalyzed allylic substitution. Angew Chem Int Ed Engl 34:462
28. Helmchen G, Pfaltz A (2000) Phosphinooxazolines-a new class of versatile, modular P, N-ligands for asymmetric catalysis. Acc Chem Res 33:336
29. Lloyd-Jones GC, Pfaltz A (1995) Synthesis and structure of low-valent tungsten complexes bearing chiral oxazoline-derived ligands. Z Naturforsch 50b:361
30. Prétǒt R, Lloyd-Jones GC, Pfaltz A (1998) Enantio- and regiocontrol in palladium- and tungsten-catalyzed allylic substitutions. Pure Appl Chem 70:1035
31. Barnes DJ, Chapman RL, Vagg RS, Watton EC (1978) Synthesis of novel bis(amides) by means of triphenyl phosphite intermediates. J Chem Eng Data 23:349
32. Trost BM, Hachiya I (1998) Asymmetric molybdenum-catalyzed alkylations. J Am Chem Soc 120:1104
33. Conlon DA, Yasuda N (2001) Practical synthesis of chiral N,Nc-Bis(2-pyridinecarboxamide)- 1,2-cyclohexane ligands. Adv Synth Catal 343:137
34. Trost BM, Hildbrand S, Dogra K (1999) Regio- and enantioselective molybdenum-catalyzed alkylations of polyenyl esters. J Am Chem Soc 121:10416
35. Belda O, Kaiser N-F, Bremberg U, Larhed M, Hallberg A, Moberg C (2000) Highly stereoand regioselective allylations catalyzed by Mo-pyridylamide complexes. Electronic and steric effects of the ligand. J Org Chem 65:5868
36. Belda O, Moberg C (2002) Substituted pyridylamide ligands in microwave-accelerated Mo (0)-catalysed allylic alkylations. Synthesis 1601
37. Belda O, Lundgren S, Moberg C (2003) Recoverable resin-supported pyridylamide ligand for microwave-accelerated molybdenum-catalyzed asymmetric allylic alkylations: Enantioselective synthesis of baclofen. Org Lett 5:2275
38. Ong J, Kerr DIB (2005) Clinical potential of GABAB receptor modulators. CNS Drug Rev 11:317
39. Malkov AV, Spoor P, Vinader V, Koĉovský P (2001) Asymmetric molybdenum(0)-catalyzed allylic substitution. Tetrahedron Lett 42:509
40. Del Litto R, Benessere V, Ruffo F, Moberg C (2009) Carbohydrate-based pyridine-2-carboxamides for Mo-catalyzed asymmetric allylic alkylations. Eur J Org Chem 1352
41. Trost BM, Dogra K, Hachiya I, Emura T, Hughes DL, Krska S, Reamer RA, Palucki M, Yasuda N, Reider PJ (2002) Designed ligands as probes for the catalytic binding mode in Mocatalyzed asymmetric allylic alkylation. Angew Chem Int Ed 41:1929
42. Glorius F, Pfaltz A (1999) Enantioselective molybdenum-catalyzed allylic alkylation using chiral bisoxazoline ligands. Org Lett 1:141
43. Glorius F, Neuburger M, Pfaltz A (2001) Highly enantio- and regioselective allylic alkylations catalyzed by chiral [bis(dihydrooxazole)] molybdenum complexes. Helv Chim Acta 84:3178
44. Trost BM, Dogra K (2002) Synthesis of novel quaternary amino acids using molybdenumcatalyzed asymmetric allylic alkylation. J Am Chem Soc 124:7256
45. Trost BM, Ariza X (1997) Catalytic asymmetric alkylation of nucleophiles: Asymmetric synthesis of a-alkylated amino acids. Angew Chem Int Ed Engl 36:2635
46. Trost BM, Dogra K, Franzini M (2004) 5H-Oxazol-4-Ones as building blocks for asymmetric synthesis of -hydroxycarboxylic acid derivatives. J Am Chem Soc 126:1944
47. Trost BM, Zhang Y (2006) Molybdenum-catalyzed asymmetric allylation of 3-alkyloxindoles: Application to the formal total synthesis of (+)-physostigmine. J Am Chem Soc 128:4590
48. Hughes DL, Lloyd-Jones GC, Krska SW, Gouriou L, Bonnet VD, Jack K, Sun Y, Mathre DJ, Reamer RA (2004) Mechanistic studies of the molybdenum-catalyzed asymmetric alkylation reaction. Proc Natl Acad Sci USA 101:5379
49. Krska SW, Hughes DL, Reamer RA, Mathre DJ, Palucki M, Yasuda N, Sun Y, Trost BM (2004) New insights into the mechanism of molybdenum-catalyzed asymmetric alkylation. Pure Appl Chem 76:625
50. Luft JAR, Yu Z-X, Hughes DL, Lloyd-Jones GC, Krska SW, Houk KN (2006) On the stability of the p-allyl intermediate in molybdenum-catalyzed asymmetric alkylations. Tetrahedron: Asymmetry 17:716
51. Krska SW, Hughes DL, Reamer RA, Mathre DJ, Sun Y, Trost BM (2002) The unusual role of CO transfer in molybdenum-catalyzed asymmetric alkylations. J Am Chem Soc 124:12656
52. Koĉovský P, Malkov AV, Vyskoĉil S ? , Lloyd-Jones GC (1999) Transition metal catalysis in organic synthesis - reflections, chirality and new vistas. Pure Appl Chem 71:1425
53. Palucki M, Um JM, Yasuda N, Conlon DA, Tsay F-R, Hartner FW, Hsiao Y, Marcune B, Karady S, Hughes DL, Dormer PG, Reider PJ (2002) Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps. J Org Chem 67:5508
54. Faller JW, Sarantopoulos N (2004) Retention of configuration and regiochemistry in allylic alkylations via the memory effect. Organometallics 23:2179
55. Conlon DA, Jensen MS, Palucki M, Yasuda N, Um JM, Yang C, Hartner FW, Tsay F-R, Hsiao Y, Pye P, Rivera NR, Hughes DL (2005) Stereoselective synthesis of an anti-HIV drug candidate. Chirality 17:149
56. Trost BM, Andersen NG (2002) Utilization of molybdenum- and palladium-catalyzed dynamic kinetic asymmetric transformations for the preparation of tertiary and quaternary stereogenic centers: A concise synthesis of tipranavir. J Am Chem Soc 124:14320
57. Trost BM, Dogra K (2007) Synthesis of (+)-D9-trans-tetrahydrocannabinol: Stereocontrol via Mo-catalyzed asymmetric allylic alkylation reaction. Org Lett 9:861