SCOPUS 정보 검색 플랫폼

Chemical Science

Volumn 5, Issue 4, 2014, Pages 1322-1327

Consecutive dynamic resolutions of phosphine oxides

(6) Kortmann, Felix A a Chang, Mu Chieh a Otten, Edwin a Couzijn, Erik P A b Lutz, Martin c Minnaard, Adriaan J a

a UNIVERSITY OF GRONINGEN (Netherlands)

b ETH ZURICH (Switzerland)

c UTRECHT UNIVERSITY (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC TRANSFORMATIONS; DYNAMIC RESOLUTION; ENANTIO; ENANTIOPURE; PHENYLPHOSPHINE OXIDES; PHOSPHINE OXIDE; SECONDARY PHOSPHINES;

CHEMISTRY;

PHOSPHORUS COMPOUNDS;

EID: 84897677607 PISSN: 20416520 EISSN: 20416539 Source Type: Journal
DOI: 10.1039/c3sc52913d Document Type: Article

Times cited : (61)

References (66)

1
- 33744543074
- L. Ackermann Synthesis 2006 1557 1571
- (2006) Synthesis , pp. 1557-1571
- Ackermann, L.¹

2
- 84858071695
- T. M. Shaikh C.-M. Weng F.-E. Hong Coord. Chem. Rev. 2012 256 771 803
- (2012) Coord. Chem. Rev. , vol.256 , pp. 771-803
- Shaikh, T.M.¹ Weng, C.-M.² Hong, F.-E.³

3
- 37649005484
- ed., Wiley-VCH
- Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications (3 Volume Set), ed., A. Börner, Wiley-VCH, 2008
- (2008) Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications (3 Volume Set)
- Börner, A.¹

4
- 1842430904
- For mixed secondary phosphine oxide-phosphines, see
- V. V. Grushin Chem. Rev. 2004 104 1629 1662
- (2004) Chem. Rev. , vol.104 , pp. 1629-1662
- Grushin, V.V.¹

5
- 77956605160
- H. Landert F. Spindler A. Wyss H.-U. Blaser B. Pugin Y. Ribourduoille B. Gschwend B. Ramalingam A. Pfaltz Angew. Chem., Int. Ed. 2010 49 6873 6876
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 6873-6876
- Landert, H.¹ Spindler, F.² Wyss, A.³ Blaser, H.-U.⁴ Pugin, B.⁵ Ribourduoille, Y.⁶ Gschwend, B.⁷ Ramalingam, B.⁸ Pfaltz, A.⁹

6
- 22144486909
- A. B. Charette A. A. Boezio A. Côté E. Moreau J. Pytkowicz J.-N. Desrosiers C. Legault Pure Appl. Chem. 2005 77 1259 1267
- (2005) Pure Appl. Chem. , vol.77 , pp. 1259-1267
- Charette, A.B.¹ Boezio, A.A.² Côté, A.³ Moreau, E.⁴ Pytkowicz, J.⁵ Desrosiers, J.-N.⁶ Legault, C.⁷

7
- 84891564839
- ed., Wiley-VCH, Weinheim, Germany
- Privileged Chiral Ligands and Catalysts, ed., Q.-L. Zhou, Wiley-VCH, Weinheim, Germany, 2011
- (2011) Privileged Chiral Ligands and Catalysts
- Zhou, Q.L.¹

8
- 0037436454
- T. P. Yoon E. N. Jacobsen Science 2003 299 1691 1693
- (2003) Science , vol.299 , pp. 1691-1693
- Yoon, T.P.¹ Jacobsen, E.N.²

9
- 84855446909
- S. Lühr J. Holz A. Börner ChemCatChem 2011 3 1708 1730
- (2011) ChemCatChem , vol.3 , pp. 1708-1730
- Lühr, S.¹ Holz, J.² Börner, A.³

10
- 77953104263
- D. R. Fandrick K. R. Fandrick J. T. Reeves Z. Tan W. Tang A. G. Capacci S. Rodriguez J. J. Song H. Lee N. K. Yee et al. J. Am. Chem. Soc. 2010 132 7600 7601
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 7600-7601
- Fandrick, D.R.¹ Fandrick, K.R.² Reeves, J.T.³ Tan, Z.⁴ Tang, W.⁵ Capacci, A.G.⁶ Rodriguez, S.⁷ Song, J.J.⁸ Lee, H.⁹ Yee, N.K.¹⁰

11
- 84875702835
- B. Mohar M. Stephan Adv. Synth. Catal. 2013 355 594 600
- (2013) Adv. Synth. Catal. , vol.355 , pp. 594-600
- Mohar, B.¹ Stephan, M.²

12
- 0037012673
- W. Tang X. Zhang Angew. Chem., Int. Ed. 2002 41 1612 1614
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1612-1614
- Tang, W.¹ Zhang, X.²

13
- 84887194203
- in, ed. C. J. Kamer and W. N. M. van Leeuwen, John Wiley & Sons, Chichester, UK, 355-389
- J. Bayardon and S. Jugé, in Phosphorus(iii) Ligands in Homogeneous Catalysis: Design and Synthesis, ed., P. C. J. Kamer, and, P. W. N. M. van Leeuwen, John Wiley & Sons, Chichester, UK, 2012, pp. 355-389
- (2012) Phosphorus(iii) Ligands in Homogeneous Catalysis: Design and Synthesis
- Bayardon, J.¹ Jugé, S.²

14
- 80054739314
- Royal Society of Chemistry, Cambridge
- A. Grabulosa, P-Stereogenic Ligands in Enantioselective Catalysis, Royal Society of Chemistry, Cambridge, 2011
- (2011) P-Stereogenic Ligands in Enantioselective Catalysis
- Grabulosa, A.¹

15
- 84903499971
- 111-141
- K. V. L. Crépy and T. Imamoto, New Aspects in Phosphorus Chemistry III, 2003, pp. 111-141
- (2003) New Aspects in Phosphorus Chemistry III
- Crépy, K.V.L.¹ Imamoto, T.²

16
- 52449134875
- Q. Xu C.-Q. Zhao L.-B. Han J. Am. Chem. Soc. 2008 130 12648 12655
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 12648-12655
- Xu, Q.¹ Zhao, C.-Q.² Han, L.-B.³

17
- 84885657780
- O. Berger J.-L. Montchamp Angew. Chem., Int. Ed. 2013 52 11377 11380
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 11377-11380
- Berger, O.¹ Montchamp, J.-L.²

18
- 0001626461
- T. Imamoto T. Oshiki T. Onozawa T. Kusumoto K. Sato J. Am. Chem. Soc. 1990 112 5244 5252
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 5244-5252
- Imamoto, T.¹ Oshiki, T.² Onozawa, T.³ Kusumoto, T.⁴ Sato, K.⁵

19
- 33947597616
- A. Grabulosa J. Granell G. Muller Coord. Chem. Rev. 2007 251 25 90
- (2007) Coord. Chem. Rev. , vol.251 , pp. 25-90
- Grabulosa, A.¹ Granell, J.² Muller, G.³

20
- 12044254595
- K. Pietrusiewicz M. Zablocka Chem. Rev. 1994 94 1375 1411
- (1994) Chem. Rev. , vol.94 , pp. 1375-1411
- Pietrusiewicz, K.¹ Zablocka, M.²

21
- 0025152027
- See also
- S. Jugé M. Stephan J. Laffitte J. Genet Tetrahedron Lett. 1990 31 6357 6360
- (1990) Tetrahedron Lett. , vol.31 , pp. 6357-6360
- Jugé, S.¹ Stephan, M.² Laffitte, J.³ Genet, J.⁴

22
- 77956611977
- For a recent and considerable extension, see
- F. Chaux S. Frynas H. Laureano C. Salomon G. Morata M.-L. Auclair M. Stephan R. Merdès P. Richard M.-J. Ondel-Eymin J.-C. Henry J. Bayardon C. Darcel S. Jugé C. R. Chim. 2010 13 1213 1226
- (2010) C. R. Chim. , vol.13 , pp. 1213-1226
- Chaux, F.¹ Frynas, S.² Laureano, H.³ Salomon, C.⁴ Morata, G.⁵ Auclair, M.-L.⁶ Stephan, M.⁷ Merdès, R.⁸ Richard, P.⁹ Ondel-Eymin, M.-J.¹⁰ Henry, J.-C.¹¹ Bayardon, J.¹² Darcel, C.¹³ Jugé, S.¹⁴

23
- 84874048569
- Z. S. Han N. Goyal M. A. Herbage J. D. Sieber B. Qu Y. Xu Z. Li J. T. Reeves J.-N. Desrosiers S. Ma N. Grinberg H. Lee H. P. R. Mangunuru Y. Zhang D. Krishnamurthy B. Z. Lu J. J. Song G. Wang C. H. Senanayake J. Am. Chem. Soc. 2013 135 2474 2477
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 2474-2477
- Han, Z.S.¹ Goyal, N.² Herbage, M.A.³ Sieber, J.D.⁴ Qu, B.⁵ Xu, Y.⁶ Li, Z.⁷ Reeves, J.T.⁸ Desrosiers, J.-N.⁹ Ma, S.¹⁰ Grinberg, N.¹¹ Lee, H.¹² Mangunuru, H.P.R.¹³ Zhang, Y.¹⁴ Krishnamurthy, D.¹⁵ Lu, B.Z.¹⁶ Song, J.J.¹⁷ Wang, G.¹⁸ Senanayake, C.H.¹⁹

24
- 0000895308
- A. R. Muci K. R. Campos D. A. Evans J. Am. Chem. Soc. 1995 117 9075 9076
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 9075-9076
- Muci, A.R.¹ Campos, K.R.² Evans, D.A.³

25
- 0034733113
- K. Nagata S. Matsukawa T. Imamoto J. Org. Chem. 2000 65 4185 4188
- (2000) J. Org. Chem. , vol.65 , pp. 4185-4188
- Nagata, K.¹ Matsukawa, S.² Imamoto, T.³

26
- 0032572094
- B. Wolfe T. Livinghouse J. Am. Chem. Soc. 1998 120 5116 5117
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 5116-5117
- Wolfe, B.¹ Livinghouse, T.²

27
- 0000107783
- K. Marsi J. Org. Chem. 1974 39 265 267
- (1974) J. Org. Chem. , vol.39 , pp. 265-267
- Marsi, K.¹

28
- 0002926693
- T. Imamoto S.-I. Kikuchi T. Miura Y. Wada Org. Lett. 2001 3 87 90
- (2001) Org. Lett. , vol.3 , pp. 87-90
- Imamoto, T.¹ Kikuchi, S.-I.² Miura, T.³ Wada, Y.⁴

29
- 11444269767
- H.-C. Wu J.-Q. Yu J. B. Spencer Org. Lett. 2004 6 4675 4678
- (2004) Org. Lett. , vol.6 , pp. 4675-4678
- Wu, H.-C.¹ Yu, J.-Q.² Spencer, J.B.³

30
- 34347405797
- M. Berthod A. Favre-Réguillon J. Mohamad G. Mignani G. Docherty M. Lemaire Synthesis 2007 1545 1548
- (2007) Synthesis , pp. 1545-1548
- Berthod, M.¹ Favre-Réguillon, A.² Mohamad, J.³ Mignani, G.⁴ Docherty, G.⁵ Lemaire, M.⁶

31
- 72449201530
- C. Petit A. Favre-Réguillon B. Albela L. Bonneviot G. Mignani M. Lemaire Organometallics 2009 28 6379 6382
- (2009) Organometallics , vol.28 , pp. 6379-6382
- Petit, C.¹ Favre-Réguillon, A.² Albela, B.³ Bonneviot, L.⁴ Mignani, G.⁵ Lemaire, M.⁶

32
- 84862198586
- Y. Li S. Das S. Zhou K. Junge M. Beller J. Am. Chem. Soc. 2012 134 9727 9732
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 9727-9732
- Li, Y.¹ Das, S.² Zhou, S.³ Junge, K.⁴ Beller, M.⁵

33
- 0000313407
- B. D. Vineyard W. S. Knowles M. J. Sabacky G. L. Bachman D. J. Weinkauff J. Am. Chem. Soc. 1977 99 5946 5952
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 5946-5952
- Vineyard, B.D.¹ Knowles, W.S.² Sabacky, M.J.³ Bachman, G.L.⁴ Weinkauff, D.J.⁵

34
- 17944370091
- J. L. Montchamp J. Organomet. Chem. 2005 690 2388 2406
- (2005) J. Organomet. Chem. , vol.690 , pp. 2388-2406
- Montchamp, J.L.¹

35
- 2642544664
- A. L. Schwan Chem. Soc. Rev. 2004 33 218 224
- (2004) Chem. Soc. Rev. , vol.33 , pp. 218-224
- Schwan, A.L.¹

36
- 84864116915
- Y.-L. Zhao G.-J. Wu Y. Li L.-X. Gao F.-S. Han Chem.-Eur. J. 2012 18 9622 9627
- (2012) Chem.-Eur. J. , vol.18 , pp. 9622-9627
- Zhao, Y.-L.¹ Wu, G.-J.² Li, Y.³ Gao, L.-X.⁴ Han, F.-S.⁵

37
- 0021208856
- Y. Xu Z. Li J. Xia H. Guo Y. Huang Synthesis 1984 781 782
- (1984) Synthesis , pp. 781-782
- Xu, Y.¹ Li, Z.² Xia, J.³ Guo, H.⁴ Huang, Y.⁵

38
- 0033807799
- R. Haynes T. Au-Yeung W. Chan W. Lam Z. Li L. Yeung A. Chan P. Li M. Koen C. Mitchell Eur. J. Org. Chem. 2000 3205 3216
- (2000) Eur. J. Org. Chem. , pp. 3205-3216
- Haynes, R.¹ Au-Yeung, T.² Chan, W.³ Lam, W.⁴ Li, Z.⁵ Yeung, L.⁶ Chan, A.⁷ Li, P.⁸ Koen, M.⁹ Mitchell, C.¹⁰

39
- 28044462224
- L. Han C. Zhao J. Org. Chem. 2005 70 10121 10123
- (2005) J. Org. Chem. , vol.70 , pp. 10121-10123
- Han, L.¹ Zhao, C.²

40
- 0030199705
- R. Haynes W. Lam L. Yeung Tetrahedron Lett. 1996 37 4729 4732
- (1996) Tetrahedron Lett. , vol.37 , pp. 4729-4732
- Haynes, R.¹ Lam, W.² Yeung, L.³

41
- 67650093199
- J. Holt A. M. Maj E. P. Schudde K. M. Pietrusiewicz L. Sieroń W. Wieczorek T. Jerphagnon I. W. C. E. Arends U. Hanefeld A. J. Minnaard Synthesis 2009 2061 2065
- (2009) Synthesis , pp. 2061-2065
- Holt, J.¹ Maj, A.M.² Schudde, E.P.³ Pietrusiewicz, K.M.⁴ Sieroń, L.⁵ Wieczorek, W.⁶ Jerphagnon, T.⁷ Arends, I.W.C.E.⁸ Hanefeld, U.⁹ Minnaard, A.J.¹⁰

42
- 0003697242
- T. Emmick R. Letsinger J. Am. Chem. Soc. 1968 90 3459 3465
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 3459-3465
- Emmick, T.¹ Letsinger, R.²

43
- 0038817811
- M. Stankevič K. M. Pietrusiewicz Synlett 2003 1012 1016
- (2003) Synlett , pp. 1012-1016
- Stankevič, M.¹ Pietrusiewicz, K.M.²

44
- 33847804694
- P. D. Henson S. B. Ockrymiek R. E. Markham J. Org. Chem. 1974 39 2296 2298
- (1974) J. Org. Chem. , vol.39 , pp. 2296-2298
- Henson, P.D.¹ Ockrymiek, S.B.² Markham, R.E.³

45
- 0000081527
- R. B. Wetzel G. L. Kenyon J. Org. Chem. 1974 39 1531 1535
- (1974) J. Org. Chem. , vol.39 , pp. 1531-1535
- Wetzel, R.B.¹ Kenyon, G.L.²

46
- 0141447907
- W. B. Farnham R. A. Lewis R. K. Murray Jr. K. Mislow J. Am. Chem. Soc. 1970 92 5808 5809
- (1970) J. Am. Chem. Soc. , vol.92 , pp. 5808-5809
- Farnham, W.B.¹ Lewis, R.A.² Murray Jr., R.K.³ Mislow, K.⁴

47
- 15944383182
- R. S. Berry J. Chem. Phys. 1960 32 933 938
- (1960) J. Chem. Phys. , vol.32 , pp. 933-938
- Berry, R.S.¹

48
- 36149028035
- R. S. Berry Rev. Mod. Phys. 1960 32 447 454
- (1960) Rev. Mod. Phys. , vol.32 , pp. 447-454
- Berry, R.S.¹

49
- 0008044667
- E. L. Muetterties J. Am. Chem. Soc. 1969 91 4115 4122
- (1969) J. Am. Chem. Soc. , vol.91 , pp. 4115-4122
- Muetterties, E.L.¹

50
- 78650625672
- E. P. A. Couzijn J. C. Slootweg A. W. Ehlers K. Lammertsma J. Am. Chem. Soc. 2010 132 18127 18140
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 18127-18140
- Couzijn, E.P.A.¹ Slootweg, J.C.² Ehlers, A.W.³ Lammertsma, K.⁴

51
- 0034697151
- Also called a Crystallization-Induced Asymmetric Transformation (CIAT), or an Asymmetric Transformation of the Second Kind. The sometimes applied term "Asymmetric Transformation of the Second Order" is a translation error and should be considered incorrect
- E. Vedejs Y. Donde J. Org. Chem. 2000 65 2337 2343
- (2000) J. Org. Chem. , vol.65 , pp. 2337-2343
- Vedejs, E.¹ Donde, Y.²

52
- 0033575396
- Unoptimized conditions, since BINOL cannot be removed with basic washing and is more expensive than DBTA
- J. Drabowicz P. Łyżwa J. Omelańczuk K. M. Pietrusiewicz M. Mikołajczyk Tetrahedron: Asymmetry 1999 10 2757 2763
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2757-2763
- Drabowicz, J.¹ Łyzwa, P.² Omelańczuk, J.³ Pietrusiewicz, K.M.⁴ Mikołajczyk, M.⁵

53
- 20344364653
- M. Stankevic K. M. Pietrusiewicz Synthesis 2005 1279 1290
- (2005) Synthesis , pp. 1279-1290
- Stankevic, M.¹ Pietrusiewicz, K.M.²

54
- 0000014251
- M. N. Glukhovtsev A. Pross M. P. McGrath L. Radom J. Chem. Phys. 1995 103 1878 1885
- (1995) J. Chem. Phys. , vol.103 , pp. 1878-1885
- Glukhovtsev, M.N.¹ Pross, A.² McGrath, M.P.³ Radom, L.⁴

55
- 75749083809
- Et al.
- Gaussian, Inc., Wallingford CT
- M. J. Frisch, et al., Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009
- (2009) Gaussian 09, Revision A.02
- Frisch, M.J.¹

56
- 0031472963
- R. K. Haynes W. W.-L. Lam I. D. Williams L.-L. Yeung Chem.-Eur. J. 1997 3 2052 2057
- (1997) Chem.-Eur. J. , vol.3 , pp. 2052-2057
- Haynes, R.K.¹ Lam, W.W.-L.² Williams, I.D.³ Yeung, L.-L.⁴

57
- 26844495597
- D. Leca L. Fensterbank E. Lacôte M. Malacria Chem. Soc. Rev. 2005 34 858 865
- (2005) Chem. Soc. Rev. , vol.34 , pp. 858-865
- Leca, D.¹ Fensterbank, L.² Lacôte, E.³ Malacria, M.⁴

58
- 29744433926
- in, ed. J. Majoral, 43-76 The SPO radical could be trapped with norbornadiene and 3,4-dihydro-2-H-pyran, see ESI. During the preparation of this manuscript, the racemization of enantiopure phosphines via a radical mechanism was reported, see
- S. Marque and P. Tordo, in Top. Curr. Chem., ed., J. P. Majoral, 2005, vol. 250, pp. 43-76
- (2005) Top. Curr. Chem. , vol.250
- Marque, S.¹ Tordo, P.²

59
- 84879527748
- A dynamic resolution of diastereomeric titanocene and zirconocene complexes, probably involving a radical mechanism, has been reported, see
- K. D. Reichl D. H. Ess A. T. Radosevich J. Am. Chem. Soc. 2013 135 9354 9357
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 9354-9357
- Reichl, K.D.¹ Ess, D.H.² Radosevich, A.T.³

60
- 0039772398
- Radical mediated dynamic kinetic resolution of amines has been reported, see
- M. Ringwald R. Stürmer H. H. Brintzinger J. Am. Chem. Soc. 1999 121 1524 1527
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 1524-1527
- Ringwald, M.¹ Stürmer, R.² Brintzinger, H.H.³

61
- 33947171039
- The use of acetaldehyde led to aldol condensation products
- S. Gastaldi S. Escoubet N. Vanthuyne G. Gil M. P. Bertrand Org. Lett. 2007 9 837 839
- (2007) Org. Lett. , vol.9 , pp. 837-839
- Gastaldi, S.¹ Escoubet, S.² Vanthuyne, N.³ Gil, G.⁴ Bertrand, M.P.⁵

62
- 0035840373
- K. Shioji Y. Ueno Y. Kurauchi Tetrahedron Lett. 2001 42 6569 6571
- (2001) Tetrahedron Lett. , vol.42 , pp. 6569-6571
- Shioji, K.¹ Ueno, Y.² Kurauchi, Y.³

63
- 84897702359
- See:, PhD thesis, Hong Kong University of Science and Technology,. For hydroxy phosphonates the reaction is well-known, see
- See: T. T.-L. Au-Yeung, PhD thesis, Hong Kong University of Science and Technology, 2001
- (2001)
- Au-Yeung, T.T.-L.¹

64
- 25444510404
- L. El Kaim L. Gaultier L. Grimaud A. Dos Santos Synlett 2005 2335 2336
- (2005) Synlett , pp. 2335-2336
- El Kaim, L.¹ Gaultier, L.² Grimaud, L.³ Dos Santos, A.⁴

65
- 0003670183
- VCH, CCDC numbers and 946519
- J. G. Verkade and L. D. Quin, Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis, VCH, 1987
- (1987) Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis
- Verkade, J.G.¹ Quin, L.D.²

66
- 0003942864
- John Wiley & Sons
- E. L. Eliel and S. H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 2008
- (2008) Stereochemistry of Organic Compounds
- Eliel, E.L.¹ Wilen, S.H.²

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