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European Journal of Organic Chemistry

Volumn , Issue 7, 2005, Pages 1354-1366

Organolithium/chiral Lewis base/BF3: A versatile combination for the enantioselective desymmetrization of meso-epoxides

(3) Vrancken, Emmanuel a Alexakis, Alexandre b Mangeney, Pierre a

a SORBONNE UNIVERSITÉ (France)

b UNIVERSITY OF GENEVA (Switzerland)

Author keywords

Boranes; Carbenoids; Lewis bases; Lithium; Synthetic methods

Indexed keywords

BORON TRIFLUORIDE; EPOXIDE; LEWIS BASE; ORGANOLITHIUM COMPOUND;

ARTICLE; ENANTIOSELECTIVITY; MECHANICS; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING;

EID: 16444374363 PISSN: 1434193X EISSN: None Source Type: Journal
DOI: 10.1002/ejoc.200400745 Document Type: Article

Times cited : (31)

References (59)

1
- 0034669636
- and references cited therein
- D. K. B. Aubrecht, M. D. Winemiller, D. B. Collum, J. Am. Chem. Soc. 2000, 122, 11084-11089 and references cited therein.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 11084-11089
- Aubrecht, D.K.B.¹ Winemiller, M.D.² Collum, D.B.³

2
- 33746442416
- For a comprehensive review see: M. C. Willis, J. Chem. Soc., Perkin Trans. 1 1999, 1765-1784.
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 1765-1784
- Willis, M.C.¹

3
- 5644297285
- (Ed.: Z. Rappoport), Wiley, Chichester
- For a general overview of the reactivity of epoxides with organolithium reagents see: F. Chemla, E. Vrancken, Patai Series: The Chemistry of Organolithium Compounds (Ed.: Z. Rappoport), Wiley, Chichester, 2004, pp. 1165-1242.
- (2004) Patai Series: The Chemistry of Organolithium Compounds , pp. 1165-1242
- Chemla, F.¹ Vrancken, E.²

4
- 0039169610
- M. Mizuno, M. Kanai, A. Iida, K. Tomioka, Tetrahedron: Asymmetry 1996, 7, 2483-2484.
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 2483-2484
- Mizuno, M.¹ Kanai, M.² Iida, A.³ Tomioka, K.⁴

5
- 0030793714
- M. Mizuno, M. Kanai, A. Iida, K. Tomioka. Tetrahedron 1997. 53, 10 699-10 708.
- (1997) Tetrahedron , vol.53
- Mizuno, M.¹ Kanai, M.² Iida, A.³ Tomioka, K.⁴

6
- 0002025799
- A. Alexakis, E. Vrancken, P. Mangeney, Synlett 1998, 1165-1166.
- (1998) Synlett , pp. 1165-1166
- Alexakis, A.¹ Vrancken, E.² Mangeney, P.³

7
- 4544248569
- A. Alexakis, A. Tomassini, S. Leconte, Tetrahedron 2004, 60, 9479-9484.
- (2004) Tetrahedron , vol.60 , pp. 9479-9484
- Alexakis, A.¹ Tomassini, A.² Leconte, S.³

8
- 0032481031
- N. Oguni, Y. Miyaai, K. Itoh, Tetrahedron Lett. 1998, 39, 9023-9026.
- (1998) Tetrahedron Lett. , vol.39 , pp. 9023-9026
- Oguni, N.¹ Miyaai, Y.² Itoh, K.³

9
- 1442335551
- C. Zhu, M. Yang, J. Sun, Y. Zhu, Y. Pan, Synlett 2004, 465-468.
- (2004) Synlett , pp. 465-468
- Zhu, C.¹ Yang, M.² Sun, J.³ Zhu, Y.⁴ Pan, Y.⁵

10
- 0001641492
- M. Yamaguchi, I. Hirao, Tetrahedron Lett. 1983, 24, 391-394.
- (1983) Tetrahedron Lett. , vol.24 , pp. 391-394
- Yamaguchi, M.¹ Hirao, I.²

11
- 0000673062
- H. C. Brown, U.S. Racheria, S. M. Singh, Tetrahedron Lett. 1984, 25, 2411-2414.
- (1984) Tetrahedron Lett. , vol.25 , pp. 2411-2414
- Brown, H.C.¹ Racheria, U.S.² Singh, S.M.³

12
- 33845469694
- M. J. Eis, J. E. Wrobel, B. Ganem, J. Am. Chem. Soc. 1984. 106, 3693-3694.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 3693-3694
- Eis, M.J.¹ Wrobel, J.E.² Ganem, B.³

13
- 0000400749
- A. Ghribi, A. Alexakis, J. F. Normant. Tetrahedron Lett. 1984, 25, 3075-3078.
- (1984) Tetrahedron Lett. , vol.25 , pp. 3075-3078
- Ghribi, A.¹ Alexakis, A.² Normant, J.F.³

14
- 0000164886
- B. H. Lipschutz, D. A. Parker, J. A. Koslowski, S. L. Ngyuen, Tetrahedron Lett. 1984, 25, 5959-5962.
- (1984) Tetrahedron Lett. , vol.25 , pp. 5959-5962
- Lipschutz, B.H.¹ Parker, D.A.² Koslowski, J.A.³ Ngyuen, S.L.⁴

15
- 0242508150
- (Ed.: D. M. Hodgson), Springer, Heidelberg
- For a general overview see: D. M. Hodgson, M. A. H. Stent, Topics in Organometallic Chemistry: Organolithiums in Enantioselective Synthesis (Ed.: D. M. Hodgson), Springer, Heidelberg, 2003, vol 5, pp. 1-21.
- (2003) Topics in Organometallic Chemistry: Organolithiums in Enantioselective Synthesis , vol.5 , pp. 1-21
- Hodgson, D.M.¹ Stent, M.A.H.²

16
- 0041078862
- P. Müller, P. Nury, Org. Lett. 2000, 2, 2845-2847.
- (2000) Org. Lett. , vol.2 , pp. 2845-2847
- Müller, P.¹ Nury, P.²

17
- 0034761267
- P. Müller, P. Nury, G. Bernardinelli, Eur. J. Org. Chem. 2001, 4137-4147.
- (2001) Eur. J. Org. Chem. , pp. 4137-4147
- Müller, P.¹ Nury, P.² Bernardinelli, G.³

18
- 0030694010
- For a review on (-)-sparteine. see: D. Hoppe, T. Hense, Angew. Chem. Int. Ed. Engl 1997, 36, 2282-2316.
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2282-2316
- Hoppe, D.¹ Hense, T.²

19
- 0001505432
- The enantiomeric excess was measured according to: A. Alexakis, S. Mutti, P. Mangeney, J. F. Normant. Tetrahedron: Asymmetry 1990, 1, 437-440.
- (1990) Tetrahedron: Asymmetry , vol.1 , pp. 437-440
- Alexakis, A.¹ Mutti, S.² Mangeney, P.³ Normant, J.F.⁴

20
- 16444363158
- note
- The absolute configuration was determined to be (1R,2S) by polarimetry and comparison of the optical rotation with the known value (see Exp. Sect.).

21
- 0032507282
- A. Thompson, E. G. Corley, M. F. Huntington, E. J. J. Grabowski, J. F. Remenar, D. B. Collum, J. Am. Chem. Soc. 1998, 120, 2028-2038.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 2028-2038
- Thompson, A.¹ Corley, E.G.² Huntington, M.F.³ Grabowski, E.J.J.⁴ Remenar, J.F.⁵ Collum, D.B.⁶

22
- 0034669286
- F. Xu, R. A. Reamer, R. Tillyer, J. M. Cummins, E. J. J. Grabowski, P. J. Reider, D. B. Collum, J. C. Huffman, J. Am. Chem. Soc. 2000, 122, 11 212-11 218.
- (2000) J. Am. Chem. Soc. , vol.122
- Xu, F.¹ Reamer, R.A.² Tillyer, R.³ Cummins, J.M.⁴ Grabowski, E.J.J.⁵ Reider, P.J.⁶ Collum, D.B.⁷ Huffman, J.C.⁸

23
- 2342476416
- T. F. Briggs, M. D. Winemiller, D. B. Collum, R. L. Parsons, Jr., A. H. Davulcu, G. D. Harris, J. M. Fortunak, P. N. Confalone, J. Am. Chem. Soc. 2004, 126, 5427-5435.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5427-5435
- Briggs, T.F.¹ Winemiller, M.D.² Collum, D.B.³ Parsons Jr., R.L.⁴ Davulcu, A.H.⁵ Harris, G.D.⁶ Fortunak, J.M.⁷ Confalone, P.N.⁸

24
- 0000149447
- J. K. Whitesell, Chem. Rev. 1992, 92, 953-964.
- (1992) Chem. Rev. , vol.92 , pp. 953-964
- Whitesell, J.K.¹

25
- 16444384597
- note
- The absolute configuration was determined to be (1R.2S) by polarimetry and comparison of the optical rotation with the known value (see Exp. Sect.).

26
- 33845376028
- B. M. Trost, J. L. Belletire, S. Godleski, P. G. McDougal, J. M. Balkovec, J. J. Baldwin, M. E. Christy, G. S. Ponticello, S. L. Varga, J. P. Springer, J. Org. Chem. 1986, 51, 2370-2374.
- (1986) J. Org. Chem. , vol.51 , pp. 2370-2374
- Trost, B.M.¹ Belletire, J.L.² Godleski, S.³ McDougal, P.G.⁴ Balkovec, J.M.⁵ Baldwin, J.J.⁶ Christy, M.E.⁷ Ponticello, G.S.⁸ Varga, S.L.⁹ Springer, J.P.¹⁰

27
- 16444364809
- A. Alexakis, E. Vrancken, P. Mangeney, J. Chem. Soc., Perkin Trans. 1 2000, 2254-3355.
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 2254-3355
- Alexakis, A.¹ Vrancken, E.² Mangeney, P.³

28
- 0242508150
- (Ed.: D. M. Hodgson), Springer, Heidelberg
- For a general overview of lithiated epoxide rearrangement, see: D. M. Hodgson, E. Gras, K. Tomooka, Topics in Organometallic Chemistry: Organolithiums in Enantioselective Synthesis (Ed.: D. M. Hodgson), Springer, Heidelberg. 2003, vol. 5, pp. 217-250.
- (2003) Topics in Organometallic Chemistry: Organolithiums in Enantioselective Synthesis , vol.5 , pp. 217-250
- Hodgson, D.M.¹ Gras, E.² Tomooka, K.³

29
- 0000723778
- A. C. Cope, H. H. Lee, H. E. Petree, J. Am. Chem. Soc. 1958, 80, 2849-2852.
- (1958) J. Am. Chem. Soc. , vol.80 , pp. 2849-2852
- Cope, A.C.¹ Lee, H.H.² Petree, H.E.³

30
- 0001117008
- J. K. Crandall, M. Apparu. Org. React. (N. Y.) 1983, 29, 345-443.
- (1983) Org. React. (N.Y.) , vol.29 , pp. 345-443
- Crandall, J.K.¹ Apparu, M.²

31
- 0001318042
- T. Satoh, Chem. Rev. 1996, 96, 3303-3325.
- (1996) Chem. Rev. , vol.96 , pp. 3303-3325
- Satoh, T.¹

32
- 0034629302
- K. M. Morgan, S. Gronert, J. Org. Chem. 2000, 65, 1461-1466.
- (2000) J. Org. Chem. , vol.65 , pp. 1461-1466
- Morgan, K.M.¹ Gronert, S.²

33
- 0033537029
- A. Ramirez, D. B. Collum, J. Am. Chem. Soc. 1999, 121, 11 114-11 121.
- (1999) J. Am. Chem. Soc. , vol.121
- Ramirez, A.¹ Collum, D.B.²

34
- 0002318553
- D. M. Hodgson, G. P. Lee, Chem. Commun. 1996, 1015-1016.
- (1996) Chem. Commun. , pp. 1015-1016
- Hodgson, D.M.¹ Lee, G.P.²

35
- 0030796218
- D. M. Hodgson. G. P. Lee, Tetrahedron: Asymmetry 1997, 8, 2303-2306.
- (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2303-2306
- Hodgson, D.M.¹ Lee, G.P.²

36
- 33748739693
- D. M. Hodgson, G. P. Lee, R. E. Marriott, A. J. Thompson, R. Wisedale, J. Withrington, J. Chem. Soc., Perkin Trans, 1 1998, 2151-2161.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 2151-2161
- Hodgson, D.M.¹ Lee, G.P.² Marriott, R.E.³ Thompson, A.J.⁴ Wisedale, R.⁵ Withrington, J.⁶

37
- 0346994914
- S. H. Wiedemann, A. Ramirez, D. B. Collum. J. Am. Chem. Soc. 2003, 125, 1583-15901.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 1583-15901
- Wiedemann, S.H.¹ Ramirez, A.² Collum, D.B.³

38
- 0036299781
- and references cited therein
- For a recent review of an asymmetric version, see: A. Magnus, S. K. Bertilsson, P. G. Andersson, Chem. Soc. Rev. 2002, 31, 223-229 and references cited therein.
- (2002) Chem. Soc. Rev. , vol.31 , pp. 223-229
- Magnus, A.¹ Bertilsson, S.K.² Andersson, P.G.³

39
- 0000705126
- J. K. Crandall, L. H. Chang, J. Org. Chem. 1967, 32, 532-536.
- (1967) J. Org. Chem. , vol.32 , pp. 532-536
- Crandall, J.K.¹ Chang, L.H.²

40
- 0000754892
- J. K. Crandall, J. Org. Chem. 1964, 29, 2830-2833.
- (1964) J. Org. Chem. , vol.29 , pp. 2830-2833
- Crandall, J.K.¹

41
- 0000419180
- J. K. Crandall, L. C. Crawley, D. B. Banks, L. C. Lin. J. Org. Chem. 1911, 36, 510-513.
- (1911) J. Org. Chem. , vol.36 , pp. 510-513
- Crandall, J.K.¹ Crawley, L.C.² Banks, D.B.³ Lin, L.C.⁴

42
- 0029942957
- D. M. Hodgson, R. Wisedale. Tetrahedron: Asymmetry 1996, 7, 1275-1276.
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1275-1276
- Hodgson, D.M.¹ Wisedale, R.²

43
- 33947330760
- J. K. Crandall, D. B. Banks, R. A. Colyer, R. J. Watkins, J. P. Arrington, J. Org. Chem. 1968, 33, 423-425.
- (1968) J. Org. Chem. , vol.33 , pp. 423-425
- Crandall, J.K.¹ Banks, D.B.² Colyer, R.A.³ Watkins, R.J.⁴ Arrington, J.P.⁵

44
- 0000267885
- M. Asami, Bull. Chem. Soc. Jpn. 1990, 63, 1402-1408.
- (1990) Bull. Chem. Soc. Jpn. , vol.63 , pp. 1402-1408
- Asami, M.¹

45
- 33746571591
- Prepared according to: A. I. Meyers, G. S. Poindexter, S. Brich, J. Org. Chem. 1978, 43, 892-898.
- (1978) J. Org. Chem. , vol.43 , pp. 892-898
- Meyers, A.I.¹ Poindexter, G.S.² Brich, S.³

46
- 0001650153
- J. K. Whitesell, R. M. Lawrence, Chimia 1986, 40, 318-321.
- (1986) Chimia , vol.40 , pp. 318-321
- Whitesell, J.K.¹ Lawrence, R.M.²

47
- 0001430466
- A Alexakis, D. Jachiet, J. F. Normant. Tetrahedron 1986, 42, 5607-5619.
- (1986) Tetrahedron , vol.42 , pp. 5607-5619
- Alexakis, A.¹ Jachiet, D.² Normant, J.F.³

48
- 16444369500
- R. K. Sehgal, R. U. Koenigsberger, T. J. Howard, J. Chem. Soc. Perkin Trans. 1 1976, 191-195.
- (1976) J. Chem. Soc. Perkin Trans. 1 , pp. 191-195
- Sehgal, R.K.¹ Koenigsberger, R.U.² Howard, T.J.³

49
- 85083266139
- J. Barluenga, F. Alvarez, J. M. Concellon, P. Bernad, M. Yus, Synthesis 1987, 318-320.
- (1987) Synthesis , pp. 318-320
- Barluenga, J.¹ Alvarez, F.² Concellon, J.M.³ Bernad, P.⁴ Yus, M.⁵

50
- 85034356760
- J. M. Barks, G. G. Weingarten, D. W. Knight, J. Chem. Soc., Perkin Trans. 1 2000, 3469-3476.
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 3469-3476
- Barks, J.M.¹ Weingarten, G.G.² Knight, D.W.³

51
- 0028289233
- D. Basavaiah, P. D. Rao, Tetrahedron: Asymmetry 1994, 5, 223-234.
- (1994) Tetrahedron: Asymmetry , vol.5 , pp. 223-234
- Basavaiah, D.¹ Rao, P.D.²

52
- 84982070913
- H. Timmerman, R. F. Rekker, W. Th. Nauta, Red Trav. Chim. Pays-Bas 1965, 84, 1348-1356.
- (1965) Red Trav. Chim. Pays-Bas , vol.84 , pp. 1348-1356
- Timmerman, H.¹ Rekker, R.F.² Nauta, W.Th.³

53
- 0009039237
- B. C. McKusick, J. Am. Chem. Soc. 1948, 70, 1976-1977.
- (1948) J. Am. Chem. Soc. , vol.70 , pp. 1976-1977
- McKusick, B.C.¹

54
- 0000778942
- F. Dumas, B. Mezrhab. J. d'Angelo, J. Org. Chem. 1996, 61, 2293-2304.
- (1996) J. Org. Chem. , vol.61 , pp. 2293-2304
- Dumas, F.¹ Mezrhab, B.² D'Angelo, J.³

55
- 16444370344
- J. W. Cook, C. L. Hewett. C. A. Lawrence, J. Chem. Soc. 1936, 71-80.
- (1936) J. Chem. Soc. , pp. 71-80
- Cook, J.W.¹ Hewett, C.L.² Lawrence, C.A.³

56
- 0001139403
- L. A. Asuncion, J. E. Baldwin, J. Org. Chem. 1995, 60, 5778-5784.
- (1995) J. Org. Chem. , vol.60 , pp. 5778-5784
- Asuncion, L.A.¹ Baldwin, J.E.²

57
- 0000318937
- H. C. Brown, J. V. N. Vara Prasad, A. K. Gupta, R. K. Bakshi, J. Org. Chem. 1987, 52, 310-311.
- (1987) J. Org. Chem. , vol.52 , pp. 310-311
- Brown, H.C.¹ Vara Prasad, J.V.N.² Gupta, A.K.³ Bakshi, R.K.⁴

58
- 0033800598
- E. S. Koltun, S. R. Kass, Synthesis 2000, 1366-1368.
- (2000) Synthesis , pp. 1366-1368
- Koltun, E.S.¹ Kass, S.R.²

59
- 0011208730
- M. Apparu, M. Barelle, Bull. Soc. Chim. Fr. 1977, 947-950.
- (1977) Bull. Soc. Chim. Fr. , pp. 947-950
- Apparu, M.¹ Barelle, M.²

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