Rigid P-chiral mono and diphosphines. Configurative stability and P-inversion barrier

Tetrahedron Asymmetry

Volumn 17, Issue 9, 2006, Pages 1355-1369

  Widhalm, Michael ^a   Brecker, Lothar ^a   Mereiter, Kurt ^b  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL; PALLADIUM; PHOSPHINE DERIVATIVE;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; OXIDATION; PRIORITY JOURNAL; RACEMIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33746800266     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.05.005     Document Type: Article

References (110)

1. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis (2002), Wiley-VCH, New York
2. Valentine Jr. D.H., and Hillhouse J.H. Synthesis (2003) 2437-2460
3. Powell M.T., Porte A.M., Reibenspies J., and Burgess K. Tetrahedron 57 (2001) 5027-5038
4. Kataoka N., Shelby Q., Stambuli J.P., and Hartwig J.F. J. Org. Chem. 67 (2002) 5553-5566
5. Colby E.A., and Jamison T.F. J. Org. Chem. 68 (2003) 156-166
6. Jensen J.F., and Johannsen M. Org. Lett. 5 (2003) 3025-3028
7. Baillie C., Zhang L., and Xiao J. J. Org. Chem. 69 (2004) 7779-7782
8. Jerphagnon T., Renaud J.-L., and Bruneau C. Tetrahedron: Asymmetry 15 (2004) 2101-2111
9. Selected papers:. Vineyard B.D., Knowles W.S., Sabacky M.J., Bachmann G.L., and Weinkauff D.J. J. Am. Chem. Soc. 99 (1977) 5946-5952
10. Johnson C.R., and Imamoto Z. J. Org. Chem. 52 (1987) 2170-2174
11. Kolodiazhnyi O.I. Tetrahedron: Asymmetry 9 (1998) 1279-1332
12. Marinetti A., Kruger V., and Buzin F.-X. Coord. Chem. Rev. 178-180 (1998) 755-770
13. Albert J., Bosque R., Cadena J.M., Delgado S., Granell J., Muller G., Ordinas J.I., Bardia M.F., and Solans X. Chem. A Eur. J. 8 (2002) 2279-2287
14. Crepy K.V.L., and Imamoto T. Tetrahedron Lett. 43 (2002) 7735-7737
15. Maienza F., Spindler F., Thommen M., Pugin B., Malan C., and Mezzetti A. J. Org. Chem. 67 (2002) 5239-5249
16. Danjo H., Sasaki W., Miyazaki T., and Imamoto T. Tetrahedron Lett. 44 (2003) 3467-3469
17. Danjo H., Higuchi M., Yada M., and Imamoto T. Tetrahedron Lett. 45 (2004) 603-606
18. Katagiri K., Danjo H., Yamaguchi K., and Imamoto T. Tetrahedron 61 (2005) 4701-4707
19. Liu D., and Zhang X. Eur. J. Org. Chem. (2005) 646-649
20. Selected papers:. Pietrusiewicz K.M., and Zablocka M. Chem. Rev. 94 (1994) 1375-1411
21. Korpiun O., Lewis R.A., Chickos J., and Mislow K. J. Am. Chem. Soc. 90 (1968) 4842-4846
22. Roberts N.K., and Wild S.B. J. Am. Chem. Soc. 101 (1979) 6254-6260
23. Valentine Jr. D., Blount J.F., and Toth K. J. Org. Chem. 45 (1980) 3691-3698
24. Jugé S., and Genet J.P. Tetrahedron Lett. 30 (1989) 2783-2786
25. Jugé S., Stephan M., Laffitte J.A., and Genet J.P. Tetrahedron Lett. 31 (1990) 6357-6360
26. Brown J.M., Carey J.V., and Russell M.J.H. Tetrahedron 46 (1990) 4877-4886
27. Jugé S., Stephan M., Merdés R., Genet J.P., and Halut-Despontes S. J. Chem. Soc., Chem. Commun. (1993) 531-533
28. Corey E.J., Chen Z., and Tanoury G.J. J. Am. Chem. Soc. 115 (1993) 11000-11001
29. Brown J.M., and Laing J.C.P. J. Organomet. Chem. 529 (1997) 435-444
30. Wolfe B., and Livinghouse T. J. Am. Chem. Soc. 120 (1998) 5116-5117
31. Imamoto T., Watanabe J., Wada Y., Masuda H., Yamada H., Tsuruta H., Matsukawa S., and Yamaguchi K. J. Am. Chem. Soc. 120 (1998) 1635-1636
32. Nagata K., Matsukawa S., and Imamoto T. J. Org. Chem. 65 (2000) 4185-4188
33. Miura T., Yamada H., Kikuchi S., and Imamoto T. J. Org. Chem. 65 (2000) 1877-1880
34. Watanabe T., Gridnev I.D., and Imamoto Z. Chirality (2000) 346-351
35. Ohashi A., and Imamoto T. Tetrahedron Lett. 42 (2001) 1099-1101
36. Wolfe B., and Livinghouse T. J. Org. Chem. 66 (2001) 1514-1516
37. Heath H., Wolfe B., Livinghouse T., and Bae S.K. Synthesis (2001) 2341-2347
38. Sugama H., Saito H., Danjo H., and Imamoto T. Synthesis (2001) 2348-2353
39. Nettekoven U., Widhalm M., Kalchhauser H., Kamer P.C.J., van Leeuwen P.W.N.M., Lutz M., and Spek A.L. J. Org. Chem. 66 (2001) 759-770
40. Imamoto T., Crépy K.V.L., and Katagiri K. Tetrahedron: Asymmetry 15 (2004) 2213-2218
41. Imamoto T., Oohara N., and Takahashi H. Synthesis (2004) 1353-1358
42. Johansson M.J., Schwartz L., Amedjkouh M., and Kann N. Tetrahedron: Asymmetry 15 (2004) 3531-3538
43. Chan V.S., Stewart I.C., Bergman R.G., and Toste F.D. J. Am. Chem. Soc. 128 (2006) 2786-2787
44. Scriban C., and Glueck D.S. J. Am. Chem. Soc. 128 (2006) 2788-2789 see also Ref. 4
45. Baechler R.D., and Mislow K. J. Am. Chem. Soc. 92 (1970) 3090-3093
46. Rauk A., Allen L.C., and Mislow K. Angew. Chem. 82 (1970) 453-468
47. Mcdonell G.D., Berlin K.D., Baker J.R., Ealick S.E., van der Helm D., and Marsi K.L. J. Am. Chem. Soc. 100 (1977) 4535-4540
48. Delaere D., Dransfeld A., Nguyen M.T., and Vanquickenborne L.G. J. Org. Chem. 65 (2000) 2631-2636
49. Alder R.W., and Read D. Angew. Chem., Int. Ed. 39 (2000) 2879-2881
50. Pelzer S., Wichmann K., Wesendrup R., and Schwerdtfeger P. J. Phys. Chem. A 106 (2002) 6387-6394
51. Hoge G. J. Am. Chem. Soc. 126 (2004) 9920-9921
52. Egan W., Tang R., Zon G., and Mislow K. J. Am. Chem. Soc. 92 (1970) 1442-1444
53. Baechler R.D., Andose J.D., Stackhouse J., and Mislow K. J. Am. Chem. Soc. 94 (1972) 8060-8065
54. Hughes A.N., and Edgecombe K.E. Heterocycles 33 (1992) 563-572
55. Nyulaszi L. J. Phys. Chem. 99 (1995) 586-591
56. For synthesis and application of dibenzophosphols see:. McEwen W.E., and Lau K.W. J. Org. Chem. 47 (1982) 3595-3596
57. Cornforth J., Cornforth R.H., and Gray R.T. J. Chem. Soc., Perkin Trans. 1 (1982) 2289-2297
58. Cornforth J., Ridley D.D., Sierakowski A.F., Uguen D., and Wallace T.W. J. Chem. Soc., Perkin Trans. 1 (1982) 2317-2323
59. Vedejs E., and Marth C. Tetrahedron Lett. 28 (1987) 3445-3448
60. Ogawa S., Tajiri Y., and Furukawa N. Bull. Chem. Soc. Jpn. 64 (1991) 3182-3184
61. Durán E., Gordo E., Granell J., Velasco D., and López-Calahorra F. Tetrahedron Lett. 42 (2001) 7791-7793
62. Chen R.-F., Fan Q.-L., Zheng C., and Huang W. Org. Lett. 8 (2006) 203-205
63. McCarthy M., and Guiry P.J. Tetrahedron 57 (2001) 3809-3844
64. Shimizu H., Nagasaki I., and Saito T. Tetrahedron 61 (2005) 5405-5432
65. Noyori R., and Takaya H. Acc. Chem. Res. 23 (1990) 345-350
66. Krizan T.D., and Martin J.C. J. Am. Chem. Soc. 105 (1983) 6155-6157
67. Toda F., Mori K., Stein Z., and Goldberg I. J. Org. Chem. 53 (1988) 308-312
68. Shibata T., Tsuruta H., Danjo H., and Imamoto T. J. Mol. Catal. A Chem. 196 (2003) 117-124
69. Drabowicz J., Lyzwa P., Omelanczuk J., Pietrusiewicz K.M., and Mikolajczyk M. Tetrahedron: Asymmetry 10 (1999) 2757-2763
70. Anderson B.A., Bell E.C., Ginah F.O., Harn N.K., Pagh L.M., and Wepsiec J.P. J. Org. Chem. 63 (1998) 8224-8228
71. Kotha S., Lahiri K., and Kashinath D. Tetrahedron 58 (2002) 9633-9695
72. Bellina F., Carpita A., and Rossi R. Synthesis (2004) 2419-2440
73. Fritzsche H., Hasserodt U., and Korte F. Chem. Ber. 97 (1964) 1988-1993
74. Fritzsche H., Hasserodt U., Korte F., Friese G., and Adrian K. Chem. Ber. 98 (1965) 171-174
75. Naumann K., Zon G., and Mislow K. J. Am. Chem. Soc. 91 (1969) 7012-7023
76. Hu W., Chen C.-C., Xue G., and Chan A.S.C. Tetrahedron: Asymmetry 9 (1998) 4183-4192
77. Griffin S., Heath L., and Wyatt P. Tetrahedron Lett. 39 (1998) 4405-4406
78. Allen Jr. A., Ma L., and Lin W. Tetrahedron Lett. 43 (2002) 3707-3710
79. Shibata T., Tsuruta H., Danjo H., and Imamoto T. J. Mol. Catal. A 196 (2003) 117-124
80. Gorobets E., Sun G.-R., Wheatley B.M.M., and Keay B.A. Tetrahedron Lett. 45 (2004) 3597-3601
81. Coumbe T., Lawrence N.J., and Muhammad F. Tetrahedron Lett. 35 (1994) 625-628
82. Imamoto T., Kikuchi S., Miura T., and Wada Y. Org. Lett. 3 (2001) 87-90
83. Wu H.-C., Yu J.-Q., and Spencer J.B. Org. Lett. 6 (2004) 4675-4678
84. Hassan J., Sévignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359-1469
85. In: Diederich F., and Stang P.J. (Eds). Metal-catalyzed Cross-coupling Reactions (1998), Wiley-VCH, Weinheim
86. Fürstner A., Leitner A., Mendéz M., and Krause H. J. Am. Chem. Soc. 124 (2002) 13856-13863
87. Scheiper B., Bonnekessel M., Krause H., and Fürstner A. J. Org. Chem. 69 (2004) 3943-3949
88. Wu S., He M., and Zhang X. Tetrahedron: Asymmetry 15 (2004) 2177-2180
89. Leroux F., Gorecka J., and Schlosser M. Synthesis (2004) 326-328
90. Sapountzis J., Lin W., Kofink C.C., Despotopoulou C., and Knochel P. Angew. Chem. 117 (2005) 1682-1685
91. Feuerstein M., Doucet H., and Santelli M. Tetrahedron Lett. 42 (2001) 6667-6670
92. Castanet A.-S., Colobert F., Broutin P.-E., and Obringer M. Tetrahedron: Asymmetry 13 (2002) 659-665
93. Smith R.C., Woloszynek R.A., Chen W., Ren T., and Protasiewicz J.D. Tetrahedron Lett. 45 (2004) 8327-8330
94. Pai C.-C., Li Y.-M., Zhou Z.-Y., and Chan A.S.C. Tetrahedron Lett. 43 (2002) 2789-2792
95. Duprat de Paule S., Jeulin S., Ratovelomanana-Vidal V., Genet J.-P., Champion N., and Dellis P. Tetrahedron Lett. 44 (2003) 823-826
96. Shimizu H., Ishizaki T., Fujiwara T., and Saito T. Tetrahedron: Asymmetry 15 (2004) 2169-2172
97. Sun Y., Wan X., Guo M., Wang D., Dong X., Pan Y., and Zhang Z. Tetrahedron: Asymmetry 15 (2004) 2185-2188
98. Baillie C., and Xiao J. Tetrahedron 60 (2004) 4159-4168
99. Gorobets E., Wheatley B.M.M., Hopkins J.M., McDonald R., and Keay B.A. Tetrahedron Lett. 46 (2005) 3843-3846
100. Hong R., Hoen R., Zhang J., and Lin G. Synlett (2001) 1527-1530
101. Lin G., and Hong R. J. Org. Chem. 66 (2001) 2877-2880
102. Holmes R.R. Acc. Chem. Res. 37 (2004) 746-753 and references cited therein
103. Chandrasekaran A., Timosheva N.V., Day R.O., and Holmes R.R. Inorg. Chem. 42 (2003) 3285-3292
104. Bishop J.J., Davison A., Katcher M.L., Lichtenberg D.W., Merrill R.E., and Smart J.C. J. Organomet. Chem. 27 (1971) 241-249
105. Venanzi L.M. J. Chem. Soc. (1958) 719-724
106. Shriner, R. L.; Neumann, F. W. Org. Synth. Coll. Vol. III 1955, 74.
107. See also:. Erdik E. Tetrahedron 43 (1987) 2203-2212
108. Zuman P., and Patel R.C. Techniques in Organic Reaction Kinetics (1984), John Wiley & Sons, New York p 102
109. Bruker. Programs smart, version 5.054; saint, version 6.2.9; sadabs version 2.10; xprep, version 5.1; shelxtl, version 5.1. Bruker AXS Inc., Madison, WI, USA, 2001.
110. Sheldrick, G. M.. Programs shelxs97 and shelxl97, University of Göttingen, Germany, 1997.