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Angewandte Chemie - International Edition

Volumn 52, Issue 20, 2013, Pages 5338-5341

Highly stereoselective synthesis of z-homoallylic alcohols by kinetic resolution of racemic secondary allyl boronates

(3) Incerti Pradillos, Celia A a Kabeshov, Mikhail A a Malkov, Andrei V a

a LOUGHBOROUGH UNIVERSITY (United Kingdom)

Author keywords

allylation; asymmetric synthesis; organocatalysis; stereoselectivity; steric effects

Indexed keywords

ALLYL HALIDES; ASYMMETRIC SYNTHESIS; BORONATES; KINETIC RESOLUTION; ORGANOCATALYSIS; STEREOSELECTIVE SYNTHESIS; STERIC EFFECT;

ALLYLATION; CATALYSIS; REACTION KINETICS; STEREOCHEMISTRY;

STEREOSELECTIVITY;

EID: 84877285356 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201300709 Document Type: Article

Times cited : (54)

References (78)

1
- 0002026625
- in (Ed.: J. Otera), Wiley-VCH, Weinheim
- S. R. Chemler, W. R. Roush, in Modern Carbonyl Chemistry (Ed.:, J. Otera,), Wiley-VCH, Weinheim, 2000, pp. 403-490
- (2000) Modern Carbonyl Chemistry , pp. 403-490
- Chemler, S.R.¹ Roush, W.R.²

2
- 0041878778
- S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763-2793
- (2003) Chem. Rev. , vol.103 , pp. 2763-2793
- Denmark, S.E.¹ Fu, J.²

3
- 0242393338
- T. Herold, R. W. Hoffmann, Angew. Chem. 1978, 90, 822-823
- (1978) Angew. Chem. , vol.90 , pp. 822-823
- Herold, T.¹ Hoffmann, R.W.²

4
- 84980145665
- Angew. Chem. Int. Ed. Engl. 1978, 17, 768-769
- (1978) Angew. Chem. Int. Ed. Engl. , vol.17 , pp. 768-769

5
- 33845550192
- H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092-2093
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 2092-2093
- Brown, H.C.¹ Jadhav, P.K.²

6
- 0000746743
- H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 293-294
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 293-294
- Brown, H.C.¹ Bhat, K.S.²

7
- 0000283253
- S. Masamune, B. Kim, J. Garcia, J. Org. Chem. 1987, 52, 4831-4832
- (1987) J. Org. Chem. , vol.52 , pp. 4831-4832
- Masamune, S.¹ Kim, B.² Garcia, J.³

8
- 0008205773
- S. Masamune, R. P. Short, J. Am. Chem. Soc. 1989, 111, 1892-1894
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 1892-1894
- Masamune, S.¹ Short, R.P.²

9
- 33845183116
- E. J. Corey, C. Yu, S. S. Kim, J. Am. Chem. Soc. 1989, 111, 5495-5496
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 5495-5496
- Corey, E.J.¹ Yu, C.² Kim, S.S.³

10
- 0000995725
- W. R. Roush, A. E. Walts, L. K. Hoong, J. Am. Chem. Soc. 1985, 107, 8186-8190
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 8186-8190
- Roush, W.R.¹ Walts, A.E.² Hoong, L.K.³

11
- 0025128154
- W. R. Roush, A. D. Palkowitz, K. Ando, J. Am. Chem. Soc. 1990, 112, 6348-6359
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 6348-6359
- Roush, W.R.¹ Palkowitz, A.D.² Ando, K.³

12
- 0001697761
- W. R. Roush, K. Ando, D. D. Powers, A. D. Palkowitz, R. L. Halterman, J. Am. Chem. Soc. 1990, 112, 6339-6348
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 6339-6348
- Roush, W.R.¹ Ando, K.² Powers, D.D.³ Palkowitz, A.D.⁴ Halterman, R.L.⁵

13
- 23944463945
- E. Canales, K. G. Prasad, J. A. Soderquist, J. Am. Chem. Soc. 2005, 127, 11572-11573; for the first allylation of aldehydes using allylboron regarents, see
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 11572-11573
- Canales, E.¹ Prasad, K.G.² Soderquist, J.A.³

14
- 34250592550
- B. M. Mikhailov, Y. N. Bubnov, Russ. Chem. Bull. 1964, 13, 1774-1776.
- (1964) Russ. Chem. Bull. , vol.13 , pp. 1774-1776
- Mikhailov, B.M.¹ Bubnov, Y.N.²

15
- 3242808098
- R. Wada, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8910-8911
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 8910-8911
- Wada, R.¹ Oisaki, K.² Kanai, M.³ Shibasaki, M.⁴

16
- 34547817162
- V. Rauniyar, D. G. Hall, Angew. Chem. 2006, 118, 2486-2488
- (2006) Angew. Chem. , vol.118 , pp. 2486-2488
- Rauniyar, V.¹ Hall, D.G.²

17
- 33746292398
- Angew. Chem. Int. Ed. 2006, 45, 2426-2428
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 2426-2428

18
- 46049109527
- V. Rauniyar, H. Zhai, D. G. Hall, J. Am. Chem. Soc. 2008, 130, 8481-8490
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 8481-8490
- Rauniyar, V.¹ Zhai, H.² Hall, D.G.³

19
- 66249089488
- V. Rauniyar, D. G. Hall, J. Org. Chem. 2009, 74, 4236-4241
- (2009) J. Org. Chem. , vol.74 , pp. 4236-4241
- Rauniyar, V.¹ Hall, D.G.²

20
- 33749514608
- S. Lou, P. N. Moquist, S. E. Schaus, J. Am. Chem. Soc. 2006, 128, 12660-12661
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 12660-12661
- Lou, S.¹ Moquist, P.N.² Schaus, S.E.³

21
- 77954247337
- D. S. Barnett, P. N. Moquist, S. E. Schaus, Angew. Chem. 2009, 121, 8835-8838
- (2009) Angew. Chem. , vol.121 , pp. 8835-8838
- Barnett, D.S.¹ Moquist, P.N.² Schaus, S.E.³

22
- 70350588841
- Angew. Chem. Int. Ed. 2009, 48, 8679-8682
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 8679-8682

23
- 77956083804
- P. Jain, J. C. Antilla, J. Am. Chem. Soc. 2010, 132, 11884-11886; for the related asymmetric propargylation, see
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 11884-11886
- Jain, P.¹ Antilla, J.C.²

24
- 79961086827
- D. S. Barnett, S. E. Schaus, Org. Lett. 2011, 13, 4020-4023
- (2011) Org. Lett. , vol.13 , pp. 4020-4023
- Barnett, D.S.¹ Schaus, S.E.²

25
- 84858215169
- P. Jain, H. Wang, K. N. Houk, J. C. Antilla, Angew. Chem. 2012, 124, 1420-1423
- (2012) Angew. Chem. , vol.124 , pp. 1420-1423
- Jain, P.¹ Wang, H.² Houk, K.N.³ Antilla, J.C.⁴

26
- 84863011869
- Angew. Chem. Int. Ed. 2012, 51, 1391-1394
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1391-1394

27
- 84863505076
- M. Chen, W. R. Roush, J. Am. Chem. Soc. 2012, 134, 10947-10952
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 10947-10952
- Chen, M.¹ Roush, W.R.²

28
- 84857209656
- L. R. Reddy, Org. Lett. 2012, 14, 1142-1145; for the related asymmetric allenylation, see
- (2012) Org. Lett. , vol.14 , pp. 1142-1145
- Reddy, L.R.¹

29
- 84865222086
- L. R. Reddy, Chem. Commun. 2012, 48, 9189-9191.
- (2012) Chem. Commun. , vol.48 , pp. 9189-9191
- Reddy, L.R.¹

30
- 0035913727
- J. Nokami, M. Ohga, H. Nakamoto, T. Matsubara, I. Hussain, K. Kataoka, J. Am. Chem. Soc. 2001, 123, 9168-9169
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 9168-9169
- Nokami, J.¹ Ohga, M.² Nakamoto, H.³ Matsubara, T.⁴ Hussain, I.⁵ Kataoka, K.⁶

31
- 4544291145
- J. Nokami, K. Nomiyama, S. Matsuda, N. Imai, K. Kataoka, Angew. Chem. 2003, 115, 1311-1314
- (2003) Angew. Chem. , vol.115 , pp. 1311-1314
- Nokami, J.¹ Nomiyama, K.² Matsuda, S.³ Imai, N.⁴ Kataoka, K.⁵

32
- 0037451435
- Angew. Chem. Int. Ed. 2003, 42, 1273-1276
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1273-1276

33
- 0013282193
- T.-P. Loh, C.-L. K. Lee, K.-T. Tan, Org. Lett. 2002, 4, 2985-2987
- (2002) Org. Lett. , vol.4 , pp. 2985-2987
- Loh, T.-P.¹ Lee, C.-L.K.² Tan, K.-T.³

34
- 60749116598
- A. V. Malkov, M. A. Kabeshov, M. Barłóg, P. Kočovský, Chem. Eur. J. 2009, 15, 1570-1573
- (2009) Chem. Eur. J. , vol.15 , pp. 1570-1573
- Malkov, A.V.¹ Kabeshov, M.A.² Barłóg, M.³ Kočovský, P.⁴

35
- 79957818248
- A. V. Malkov, O. Kysilka, M. Edgar, A. Kadlčíková, M. Kotora, P. Kočovský, Chem. Eur. J. 2011, 17, 7162-7166.
- (2011) Chem. Eur. J. , vol.17 , pp. 7162-7166
- Malkov, A.V.¹ Kysilka, O.² Edgar, M.³ Kadlčíková, A.⁴ Kotora, M.⁵ Kočovský, P.⁶

36
- 76349126369
- S. Kobayashi, T. Endo, U. Schneider, M. Ueno, Chem. Commun. 2010, 46, 1260-1262
- (2010) Chem. Commun. , vol.46 , pp. 1260-1262
- Kobayashi, S.¹ Endo, T.² Schneider, U.³ Ueno, M.⁴

37
- 84871012245
- S. Kobayashi, T. Endo, M. Ueno, Angew. Chem. 2011, 123, 12470-12473
- (2011) Angew. Chem. , vol.123 , pp. 12470-12473
- Kobayashi, S.¹ Endo, T.² Ueno, M.³

38
- 83755196032
- Angew. Chem. Int. Ed. 2011, 50, 12262-12265.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 12262-12265

39
- 11144266593
- J. Pietruszka, N. Schone, Angew. Chem. 2003, 115, 5796-5799
- (2003) Angew. Chem. , vol.115 , pp. 5796-5799
- Pietruszka, J.¹ Schone, N.²

40
- 0345530071
- Angew. Chem. Int. Ed. 2003, 42, 5638-5641
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5638-5641

41
- 67649403223
- E. Fernandez, J. Pietruszka, Synlett 2009, 1474-1476
- (2009) Synlett , pp. 1474-1476
- Fernandez, E.¹ Pietruszka, J.²

42
- 53849130112
- L. Carosi, D. G. Hall, Angew. Chem. 2007, 119, 6017-6019
- (2007) Angew. Chem. , vol.119 , pp. 6017-6019
- Carosi, L.¹ Hall, D.G.²

43
- 34547814662
- Angew. Chem. Int. Ed. 2007, 46, 5913-5915
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5913-5915

44
- 35048817308
- G. Y. Fang, V. K. Aggarwal, Angew. Chem. 2007, 119, 363-366
- (2007) Angew. Chem. , vol.119 , pp. 363-366
- Fang, G.Y.¹ Aggarwal, V.K.²

45
- 33846436053
- Angew. Chem. Int. Ed. 2007, 46, 359-362
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 359-362

46
- 77949826633
- M. Althaus, A. Mahmood, J. R. Suárez, S. P. Thomas, V. K. Aggarwal, J. Am. Chem. Soc. 2010, 132, 4025-4028
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 4025-4028
- Althaus, M.¹ Mahmood, A.² Suárez, J.R.³ Thomas, S.P.⁴ Aggarwal, V.K.⁵

47
- 77955388332
- A. Guzman-Martinez, A. H. Hoveyda, J. Am. Chem. Soc. 2010, 132, 10634-10637
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 10634-10637
- Guzman-Martinez, A.¹ Hoveyda, A.H.²

48
- 28044443673
- H. Ito, C. Kawakami, M. Sawamura, J. Am. Chem. Soc. 2005, 127, 16034-16035
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 16034-16035
- Ito, H.¹ Kawakami, C.² Sawamura, M.³

49
- 36849074311
- H. Ito, S. Ito, Y. Sasaki, K. Matsuura, M. Sawamura, J. Am. Chem. Soc. 2007, 129, 14856-14857
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 14856-14857
- Ito, H.¹ Ito, S.² Sasaki, Y.³ Matsuura, K.⁴ Sawamura, M.⁵

50
- 78049329370
- H. Ito, S. Kunii, M. Sawamura, Nat. Chem. 2010, 2, 972-976
- (2010) Nat. Chem. , vol.2 , pp. 972-976
- Ito, H.¹ Kunii, S.² Sawamura, M.³

51
- 84859523565
- H. Ito, T. Miya, M. Sawamura, Tetrahedron 2011, 68, 3423-3437
- (2011) Tetrahedron , vol.68 , pp. 3423-3437
- Ito, H.¹ Miya, T.² Sawamura, M.³

52
- 67649964459
- H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 9134-9135
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 9134-9135
- Burks, H.E.¹ Kliman, L.T.² Morken, J.P.³

53
- 79952267124
- J. K. Park, H. H. Lackey, B. A. Ondrusek, D. T. McQuade, J. Am. Chem. Soc. 2011, 133, 2410-2413.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 2410-2413
- Park, J.K.¹ Lackey, H.H.² Ondrusek, B.A.³ McQuade, D.T.⁴

54
- 77953598605
- M. Chen, W. R. Roush, Org. Lett. 2010, 12, 2706-2709
- (2010) Org. Lett. , vol.12 , pp. 2706-2709
- Chen, M.¹ Roush, W.R.²

55
- 77957154288
- S. M. Winbush, W. R. Roush, Org. Lett. 2010, 12, 4344-4347
- (2010) Org. Lett. , vol.12 , pp. 4344-4347
- Winbush, S.M.¹ Roush, W.R.²

56
- 33947380529
- F. Peng, D. G. Hall, J. Am. Chem. Soc. 2007, 129, 3070-3071
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 3070-3071
- Peng, F.¹ Hall, D.G.²

57
- 44649165603
- D. G. Hall, Pure Appl. Chem. 2008, 80, 913-927
- (2008) Pure Appl. Chem. , vol.80 , pp. 913-927
- Hall, D.G.¹

58
- 11144268940
- J. Pietruszka, N. Schone, Eur. J. Org. Chem. 2004, 5011-5019
- (2004) Eur. J. Org. Chem. , pp. 5011-5019
- Pietruszka, J.¹ Schone, N.²

59
- 53849108486
- J. Pietruszka, N. Schone, W. Frey, L. Grundl, Chem. Eur. J. 2008, 14, 5178-5197.
- (2008) Chem. Eur. J. , vol.14 , pp. 5178-5197
- Pietruszka, J.¹ Schone, N.² Frey, W.³ Grundl, L.⁴

60
- 0002555436
- R. W. Hoffmann, B. Landmann, Tetrahedron Lett. 1983, 24, 3209-3212
- (1983) Tetrahedron Lett. , vol.24 , pp. 3209-3212
- Hoffmann, R.W.¹ Landmann, B.²

61
- 0008384235
- R. W. Hoffmann, B. Landmann, Angew. Chem. 1984, 96, 427-428
- (1984) Angew. Chem. , vol.96 , pp. 427-428
- Hoffmann, R.W.¹ Landmann, B.²

62
- 84985510273
- Angew. Chem. Int. Ed. Engl. 1984, 23, 437-438
- (1984) Angew. Chem. Int. Ed. Engl. , vol.23 , pp. 437-438

63
- 0001113711
- R. W. Hoffmann, B. Landmann, Angew. Chem. 1986, 98, 186-187
- (1986) Angew. Chem. , vol.98 , pp. 186-187
- Hoffmann, R.W.¹ Landmann, B.²

64
- 84985502387
- Angew. Chem. Int. Ed. Engl. 1986, 25, 189-190
- (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 189-190

65
- 84961499881
- R. W. Hoffmann, Pure Appl. Chem. 1988, 60, 123-130
- (1988) Pure Appl. Chem. , vol.60 , pp. 123-130
- Hoffmann, R.W.¹

66
- 84985687565
- R. W. Hoffmann, J. J. Wolff, Chem. Ber. 1991, 124, 563-569.
- (1991) Chem. Ber. , vol.124 , pp. 563-569
- Hoffmann, R.W.¹ Wolff, J.J.²

67
- 2542429225
- J. Nokami, K. Nomiyama, S. Matsuda, S. M. Shafi, K. Kataoka, Org. Lett. 2004, 6, 1261-1264
- (2004) Org. Lett. , vol.6 , pp. 1261-1264
- Nokami, J.¹ Nomiyama, K.² Matsuda, S.³ Shafi, S.M.⁴ Kataoka, K.⁵

68
- 2542422725
- C.-L. K. Lee, C.-H. A. Lee, K.-T. Tan, T.-P. Loh, Org. Lett. 2004, 6, 1281-1283.
- (2004) Org. Lett. , vol.6 , pp. 1281-1283
- Lee, C.-L.K.¹ Lee, C.-H.A.² Tan, K.-T.³ Loh, T.-P.⁴

69
- 85025762635
- R. W. Hoffmann, U. Weidmann, J. Organomet. Chem. 1980, 195, 137-146.
- (1980) J. Organomet. Chem. , vol.195 , pp. 137-146
- Hoffmann, R.W.¹ Weidmann, U.²

70
- 85050296727
- H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249-330
- (1988) Top. Stereochem. , vol.18 , pp. 249-330
- Kagan, H.B.¹ Fiaud, J.C.²

71
- 0002178750
- J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 5-26
- (2001) Adv. Synth. Catal. , vol.343 , pp. 5-26
- Keith, J.M.¹ Larrow, J.F.² Jacobsen, E.N.³

72
- 0038061857
- D. E. J. E. Robinson, S. D. Bull, Tetrahedron: Asymmetry 2005, 14, 1407-1446; for our previous report on combining enantiofacial discrimination with dynamic kinetic resolution, see
- (2005) Tetrahedron: Asymmetry , vol.14 , pp. 1407-1446
- Robinson, D.E.J.E.¹ Bull, S.D.²

73
- 53849083142
- A. V. Malkov, S. Stončius, K. Vranková, M. Arndt, P. Kočovský, Chem. Eur. J. 2008, 14, 8082-8085.
- (2008) Chem. Eur. J. , vol.14 , pp. 8082-8085
- Malkov, A.V.¹ Stončius, S.² Vranková, K.³ Arndt, M.⁴ Kočovský, P.⁵

74
- 77956019829
- M. Klussmann, L. Ratjen, S. Hoffmann, V. Wakchaure, R. Goddard, B. List, Synlett 2010, 2189-2192.
- (2010) Synlett , pp. 2189-2192
- Klussmann, M.¹ Ratjen, L.² Hoffmann, S.³ Wakchaure, V.⁴ Goddard, R.⁵ List, B.⁶

75
- 84856716075
- M. A. Grayson, S. P. Pellegrinet, J. M. Goodman, J. Am. Chem. Soc. 2012, 134, 2716-2722; for the mechanism of Lewis acid catalysis, see
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 2716-2722
- Grayson, M.A.¹ Pellegrinet, S.P.² Goodman, J.M.³

76
- 51949119636
- K. Sakata, H. Fujimoto, J. Am. Chem. Soc. 2008, 130, 12519-12526; for the most recent contribution, see Ref. [2i] and
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 12519-12526
- Sakata, K.¹ Fujimoto, H.²

77
- 84877303956
- DOI
- H. Wang, P. Jain, J. C. Antilla, K. N. Houk, J. Org. Chem. 2013, DOI:.
- (2013) J. Org. Chem.
- Wang, H.¹ Jain, P.² Antilla, J.C.³ Houk, K.N.⁴

78
- 82255160630
- J. W. Clary, T. J. Rettenmaier, R. Snelling, W. Bryks, J. Banwell, W. T. Wipke, B. Singaram, J. Org. Chem. 2011, 76, 9602-9610; for details, see the Supporting Information.
- (2011) J. Org. Chem. , vol.76 , pp. 9602-9610
- Clary, J.W.¹ Rettenmaier, T.J.² Snelling, R.³ Bryks, W.⁴ Banwell, J.⁵ Wipke, W.T.⁶ Singaram, B.⁷

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