Organocatalytic stereoisomerization versus alkene isomerization: Catalytic asymmetric synthesis of 1-hydroxy-trans -2,5-diphenylphospholane 1-oxide

Synthesis (Germany)

Volumn 45, Issue 3, 2013, Pages 308-325

  Hintermann, Lukas ^a   Schmitz, Marco ^a   Maltsev, Olegv ^a   Naumov, Panče ^b,c  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b NEW YORK UNIVERSITY ABU DHABI   (United Arab Emirates)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

asymmetric catalysis; heterocycles; isomerization; phosphorus; stereoselective synthesis

Indexed keywords

ALUMINUM TRICHLORIDE; ARYLATIONS; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; BIFUNCTIONAL; BUILDING BLOCKES; CINCHONA ALKALOID; HETEROCYCLES; ORGANOCATALYSTS; ORGANOCATALYTIC; PROTON ABSTRACTION; QUANTITATIVE YIELDS; STEREOSELECTIVE SYNTHESIS; STRUCTURAL CHANGE; SUBSTRATE RANGE; TOTAL SYNTHESIS;

ALUMINUM; CATALYSIS; DEUTERIUM; HYDROGENATION; HYDROLYSIS; ISOMERS; OLEFINS; PHOSPHORUS; STEREOCHEMISTRY; STEREOSELECTIVITY; SUBSTRATES; SYNTHESIS (CHEMICAL); THIOPHENE;

ISOMERIZATION;

1 (DIETHYLAMINO) 1 OXO 2,5 DIPHENYL 2,5 DIHYDRO 1H PHOSPHOLE; 1 (DIETHYLAMINO) 1 OXO 2,5 DIPHENYL 4,5 DIHYDRO 1H PHOSPHOLE; 1 (DIETHYLAMINO) 1 OXO 2,5 DIPHENYLPHOSPHOLANE; 1 HYDROXY 1 OXO 2,5 DIPHENYL 2,5 DIHYDRO 1H PHOSPHOLE; 1 HYDROXY 1 OXO 2,5 DIPHENYL 4,5 DIHYDRO 1H PHOSPHOLE; 1 HYDROXY 1 OXO 2,5 DIPHENYLPHOSPHOLANE; 1 HYDROXY 2,5 DIPHENYLPHOSPHOLAN 1 OXIDE; PHOSPHOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKENE ISOMERIZATION; ARTICLE; ASYMMETRIC SYNTHESIS; CONTROLLED STUDY; CYCLOADDITION; HYDROGENATION; HYDROLYSIS KINETICS; INTERMETHOD COMPARISON; ISOMERIZATION; ORGANOCATALYTIC STEREOISOMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 84872972940     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316835     Document Type: Article

References (52)

1. Larsen C. R., Grotjahn D. B. J. Am. Chem. Soc.: 2012; 134 10357
2. Frauenrath H., Brethauer D., Reim S., Maurer M., Raabe G. Angew. Chem. Int. Ed.: 2001; 40 177
3. Fu G. In Modern Rhodium-Catalyzed Organic Reactions. Evans P. A. Wiley-VCH Weinheim: 2005
4. Akutagawa S. Top. Catal.: 1997; 4 271
5. Otsuka S., Tani K. Synthesis: 1991; 665
6. Mantilli L., Mazet C. Chem. Lett.: 2010; 40 341
7. Uma R., Crévisy C., Grée R. Chem. Rev.: 2003; 103 27
8. Van der Drift R. C., Bouwman E., Drent E. J. Organomet. Chem.: 2002; 650 1
9. Inoue S., Takaya H., Tani K., Otsuka S., Sato T., Noyori R. J. Am. Chem. Soc.: 1990; 112 4897
10. Tani K., Yamagata T., Akutagawa S., Kumobayashi H., Taketomi T., Takaya H., Miyashita A., Noyori R., Otsuka S. J. Am. Chem. Soc.: 1984; 106 5208
11. Liu H., Leow D., Huang K.-W, Tan C.-H. J. Am. Chem. Soc.: 2009; 131 7212
12. Oku M., Arai S., Katayama K., Shioiri T. Synlett: 2000; 493
13. Inokuma T., Furukawa M., Suzuki Y., Kimachi T., Kobayashi Y., Takemoto Y. ChemCatChem: 2012; 4 983
14. Jacobs T. L., Dankner D. J. Org. Chem.: 1957; 22 1424
15. Hintermann L. In Asymmetric Synthesis - More Methods and Applications. Christmann M., Bräse S. Wiley-VCH Weinheim: 2012; 109
16. Hintermann L., Dittmer C. Eur. J. Org. Chem.: 2012; 5573
17. Guillen F., Fiaud J.-C. Tetrahedron Lett.: 1999; 40 2939
18. Guillen F., Rivard M., Toffano M., Legros J.-Y, Daran J.-C, Fiaud J.-C. Tetrahedron: 2002; 58 5895
19. Fiaud J.-C, Legros J.-Y. Tetrahedron Lett.: 1991; 32 5089
20. Guillen F., Moinet C., Fiaud J.-C. Bull. Soc. Chim. Fr.: 1997; 134 371
21. For a related asymmetric alkylation approach: Blake A. J., Hume S. C., Li W.-S, Simpkins N. S. Tetrahedron: 2002; 58 4589
22. McCormack W. B. US 2663737: 1953
23. McCormack W. B. Org. Synth.: 1963; 43 73
24. Campbell I. G. M, Cookson R. C., Hocking M. B., Hughes A. N. J. Chem. Soc.: 1965; 2184
25. Ezzell B. R., Freedman L. D. J. Org. Chem.: 1970; 35 241
26. Lukas B., Roberts R. M. G, Silver J., Wells A. S. J. Organomet. Chem.: 1983; 256 103
27. Cowley A. H., Kemp R. A., Lasch J. G., Norman N. C., Stewart C. A. J. Am. Chem. Soc.: 1983; 105 7444
28. Cowley A. H., Kemp R. A., Lasch J. G., Norman N. C., Stewart C. A., Whittlesey B. R., Wright T. C. Inorg. Chem.: 1986; 25 740
29. SooHoo C. K., Baxter S. G. J. Am. Chem. Soc.: 1983; 105 7443
30. Polniaszek R. P. J. Org. Chem.: 1982; 57 5189
31. King R. B., Sadanani N. D. Synth. React. Inorg. Met.-Org. Chem.: 1985; 15 149
32. Issleib K., Seidel W. Chem. Ber.: 1959; 92 2681
33. Wang G.-W, Lu Q.-Q, Xia J.-J. Eur. J. Org. Chem.: 2011; 4429
34. Seiser T., Cramer N. Chem. Eur. J.: 2010; 16 3383
35. Smith A. B., Kingery-Wood J., Leenay T. L., Nolen E. G., Sunazuka T. J. Am. Chem. Soc.: 1992; 114 1438
36. Wenkert E., Greenberg R. S., Kim H.-S. Helv. Chim. Acta: 1987; 70 2159
37. Carter M. J., Fleming I., Percival A. J. Chem. Soc., Perkin Trans. 1: 1981; 2415
38. Alder K., Günzl-Schumacher M. Chem. Ber.: 1959; 92 822
39. Keglevich G., Forintos H., Keseru G. M., Hegedus L., Toke L. Tetrahedron: 2000; 56 4823
40. Tolmachev A. A., Ivonin S. P., Kharchenko A. V., Lampeka R. D., Kozlov E. S. J. Gen. Chem. USSR (Engl. Transl.): 1991; 61 852
41. Kappe O. Angew. Chem. Int. Ed.: 2004; 43 6250
42. Loupy A. Microwaves in Organic Synthesis. Wiley-VCH Weinheim: 2002
43. Connon S. J. Chem. Commun.: 2008; 2499
44. Okino T., Hoashi Y., Takemoto Y. J. Am. Chem. Soc.: 2003; 125 12672
45. Duhaime R. M., Weedon A. C. J. Am. Chem. Soc.: 1987; 109 2479
46. Malhotra S. K., Ringold H. J. J. Am. Chem. Soc.: 1965; 87 3228
47. Hols J., Gensow M.-N, Zayas O., Börner A. Curr. Org. Chem.: 2007; 11 61
48. Galland A., Paris J. M., Schlama T., Guillot R., Fiaud J.-C, Toffano M. Eur. J. Org. Chem.: 2007; 863
49. Pilkington C. J., Zanotti-Gerosa A. Org. Lett.: 2003; 5 1273
50. Jackson M., Lennon I. C. Tetrahedron Lett.: 2007; 48 1831
51. Dobrota C., Toffano M., Fiaud J.-C. Tetrahedron Lett.: 2004; 45 8153
52. Fox M. E., Jackson M., Lennon I. C., Klosin J., Abboud K. A. J. Org. Chem.: 2008; 73 775