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Angewandte Chemie - International Edition

Volumn 54, Issue 30, 2015, Pages 8814-8818

Boron-Catalyzed Regioselective Deoxygenation of Terminal 1,2-Diols to 2-Alkanols Enabled by the Strategic Formation of a Cyclic Siloxane Intermediate

(2) Drosos, Nikolaos a Morandi, Bill a

a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG (Germany)

Author keywords

boron; cyclic intermediates; deoxygenation; diols; silanes

Indexed keywords

SILANES;

ANTI-INFLAMMATORY DRUGS; CATALYTIC ASYMMETRIC REACTIONS; CYCLIC INTERMEDIATES; DEOXYGENATIONS; DIOLS; ENANTIOMERIC EXCESS; STRUCTURAL COMPLEXITY; TRANSIENT FORMATION;

BORON;

EID: 84945155913 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201503172 Document Type: Article

Times cited : (56)

References (69)

1
- 84858049818
- A. M. Ruppert, K. Weinberg, R. Palkovits, Angew. Chem. Int. Ed. 2012, 51, 2564-2601;
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 2564-2601
- Ruppert, A.M.¹ Weinberg, K.² Palkovits, R.³

2
- 84864672645
- Angew. Chem. 2012, 124, 2614-2654;
- (2012) Angew. Chem. , vol.124 , pp. 2614-2654

3
- 77955035656
- F. M. A. Geilen, B. Engendahl, A. Harwardt, W. Marquardt, J. Klankermayer, W. Leitner, Angew. Chem. Int. Ed. 2010, 49, 5510-5514;
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 5510-5514
- Geilen, F.M.A.¹ Engendahl, B.² Harwardt, A.³ Marquardt, W.⁴ Klankermayer, J.⁵ Leitner, W.⁶

4
- 79955627599
- Angew. Chem. 2010, 122, 5642-5646;
- (2010) Angew. Chem. , vol.122 , pp. 5642-5646

5
- 34447129755
- A. Corma, S. Iborra, A. Velty, Chem. Rev. 2007, 107, 2411-2502;
- (2007) Chem. Rev. , vol.107 , pp. 2411-2502
- Corma, A.¹ Iborra, S.² Velty, A.³

6
- 79955384083
- A. G. Sergeev, J. F. Hartwig, Science 2011, 332, 439-443;
- (2011) Science , vol.332 , pp. 439-443
- Sergeev, A.G.¹ Hartwig, J.F.²

7
- 77956449471
- J. M. Nichols, L. M. Bishop, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2010, 132, 12554;
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 12554
- Nichols, J.M.¹ Bishop, L.M.² Bergman, R.G.³ Ellman, J.A.⁴

8
- 67749133709
- J. Yang, P. S. White, M. Brookhart, J. Am. Chem. Soc. 2008, 130, 17509;
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 17509
- Yang, J.¹ White, P.S.² Brookhart, M.³

9
- 77955345917
- A. Berkefeld, W. E. Piers, M. Parvez, J. Am. Chem. Soc. 2010, 132, 10660-10661.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 10660-10661
- Berkefeld, A.¹ Piers, W.E.² Parvez, M.³

10
- 0037138704
- S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 1307-1315
- Schaus, S.E.¹ Brandes, B.D.² Larrow, J.F.³ Tokunaga, M.⁴ Hansen, K.B.⁵ Gould, A.E.⁶ Furrow, M.E.⁷ Jacobsen, E.N.⁸

11
- 0030860279
- M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938;
- (1997) Science , vol.277 , pp. 936-938
- Tokunaga, M.¹ Larrow, J.F.² Kakiuchi, F.³ Jacobsen, E.N.⁴

12
- 4444276636
- for selected examples of recent synthetic strategies to prepare enantiopure terminal diols, see
- H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; for selected examples of recent synthetic strategies to prepare enantiopure terminal diols, see:
- (1994) Chem. Rev. , vol.94 , pp. 2483-2547
- Kolb, H.C.¹ VanNieuwenhze, M.S.² Sharpless, K.B.³

13
- 70349991011
- R. Kadyrov, D. Voigtlaender, R. M. Koenigs, C. Brinkmann, M. Rueping, Angew. Chem. Int. Ed. 2009, 48, 7556-7559;
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7556-7559
- Kadyrov, R.¹ Voigtlaender, D.² Koenigs, R.M.³ Brinkmann, C.⁴ Rueping, M.⁵

14
- 84858263721
- Angew. Chem. 2009, 121, 7693-7696;
- (2009) Angew. Chem. , vol.121 , pp. 7693-7696

15
- 84922768688
- J. H. Kim, I. Čoric, C. Palumbo, B. List, J. Am. Chem. Soc. 2015, 137, 1778-1781.
- (2015) J. Am. Chem. Soc. , vol.137 , pp. 1778-1781
- Kim, J.H.¹ Čoric, I.² Palumbo, C.³ List, B.⁴

16
- 84864772405
- M. Shiramizu, F. D. Toste, Angew. Chem. Int. Ed. 2012, 51, 8082-8086;
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8082-8086
- Shiramizu, M.¹ Toste, F.D.²

17
- 84869469622
- Angew. Chem. 2012, 124, 8206-8210;
- (2012) Angew. Chem. , vol.124 , pp. 8206-8210

18
- 84888622276
- M. Shiramizu, F. D. Toste, Angew. Chem. Int. Ed. 2013, 52, 12905-12909;
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 12905-12909
- Shiramizu, M.¹ Toste, F.D.²

19
- 84906049278
- Angew. Chem. 2013, 125, 13143-13147;
- (2013) Angew. Chem. , vol.125 , pp. 13143-13147

20
- 77955804248
- E. Arceo, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2010, 132, 11408-11409;
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 11408-11409
- Arceo, E.¹ Ellman, J.A.² Bergman, R.G.³

21
- 70350451288
- J. E. Ziegler, M. J. Zdilla, A. J. Evans, M. M. Abu-Omar, Inorg. Chem. 2009, 48, 9998-10000;
- (2009) Inorg. Chem. , vol.48 , pp. 9998-10000
- Ziegler, J.E.¹ Zdilla, M.J.² Evans, A.J.³ Abu-Omar, M.M.⁴

22
- 84882643636
- G. Chapman, Jr., K. M. Nicholas, Chem. Commun. 2013, 49, 8199-8201.
- (2013) Chem. Commun. , vol.49 , pp. 8199-8201
- Chapman, G.¹ Nicholas, K.M.²

23
- 84893466887
- L. L. Adduci, M. P. McLaughlin, T. A. Bender, M. R. Gagné, Angew. Chem. Int. Ed. 2014, 53, 1646-1649;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 1646-1649
- Adduci, L.L.¹ McLaughlin, M.P.² Bender, T.A.³ Gagné, M.R.⁴

24
- 84947862671
- Angew. Chem. 2014, 126, 1672-1675;
- (2014) Angew. Chem. , vol.126 , pp. 1672-1675

25
- 84873850953
- M. P. McLaughlin, L. L. Adduci, J. J. Becker, M. R. Gagné, J. Am. Chem. Soc. 2013, 135, 1225-1227;
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 1225-1227
- McLaughlin, M.P.¹ Adduci, L.L.² Becker, J.J.³ Gagné, M.R.⁴

26
- 84877307150
- T. Robert, M. Oestreich, Angew. Chem. Int. Ed. 2013, 52, 5216-5218;
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 5216-5218
- Robert, T.¹ Oestreich, M.²

27
- 84886799554
- Angew. Chem. 2013, 125, 5324-5326.
- (2013) Angew. Chem. , vol.125 , pp. 5324-5326

28
- 0033544810
- V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 8919-8922;
- (1999) Tetrahedron Lett. , vol.40 , pp. 8919-8922
- Gevorgyan, V.¹ Liu, J.-X.² Rubin, M.³ Benson, S.⁴ Yamamoto, Y.⁵

29
- 0034703322
- V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto, J. Org. Chem. 2000, 65, 6179-6186;
- (2000) J. Org. Chem. , vol.65 , pp. 6179-6186
- Gevorgyan, V.¹ Rubin, M.² Benson, S.³ Liu, J.-X.⁴ Yamamoto, Y.⁵

30
- 0034685977
- D. J. Parks, J. M. Blackwell, W. E. Piers, J. Org. Chem. 2000, 65, 3090-3098;
- (2000) J. Org. Chem. , vol.65 , pp. 3090-3098
- Parks, D.J.¹ Blackwell, J.M.² Piers, W.E.³

31
- 33745634089
- R. D. Nimmagadda, C. McRae, Tetrahedron Lett. 2006, 47, 5755-5758;
- (2006) Tetrahedron Lett. , vol.47 , pp. 5755-5758
- Nimmagadda, R.D.¹ McRae, C.²

32
- 84890827229
- E. Feghali, T. Cantat, Chem. Commun. 2014, 50, 862-865.
- (2014) Chem. Commun. , vol.50 , pp. 862-865
- Feghali, E.¹ Cantat, T.²

33
- 84863393881
- P. A. Jordan, S. J. Miller, Angew. Chem. Int. Ed. 2012, 51, 2907-2911;
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 2907-2911
- Jordan, P.A.¹ Miller, S.J.²

34
- 84867771177
- Angew. Chem. 2012, 124, 2961-2965;
- (2012) Angew. Chem. , vol.124 , pp. 2961-2965

35
- 41149131795
- references therein
- M. Sánchez-Rosellõ, A. L. A. Puchlopek, A. J. Morgan, S. J. Miller, J. Org. Chem. 2008, 73, 1774-1782, and references therein.
- (2008) J. Org. Chem. , vol.73 , pp. 1774-1782
- Sánchez-Rosellõ, M.¹ Puchlopek, A.L.A.² Morgan, A.J.³ Miller, S.J.⁴

36
- 84861814525
- T. J. AhmedFoskey, D. M. Heinekey, K. I. Goldberg, ACS Catal. 2012, 2, 1285-1289;
- (2012) ACS Catal. , vol.2 , pp. 1285-1289
- AhmedFoskey, T.J.¹ Heinekey, D.M.² Goldberg, K.I.³

37
- 63349096039
- M. Schlaf, P. Ghosh, P. J. Fagan, E. Hauptman, R. M. Bullock, Adv. Synth. Catal. 2009, 351, 789-800;
- (2009) Adv. Synth. Catal. , vol.351 , pp. 789-800
- Schlaf, M.¹ Ghosh, P.² Fagan, P.J.³ Hauptman, E.⁴ Bullock, R.M.⁵

38
- 0035887196
- M. Schlaf, P. Ghosh, P. J. Fagan, E. Hauptman, R. MorrisBullock, Angew. Chem. Int. Ed. 2001, 40, 3887-3890;
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3887-3890
- Schlaf, M.¹ Ghosh, P.² Fagan, P.J.³ Hauptman, E.⁴ MorrisBullock, R.⁵

39
- 2942553557
- Angew. Chem. 2001, 113, 4005-4008.
- (2001) Angew. Chem. , vol.113 , pp. 4005-4008

40
- 0001108843
- A. Shanzer, Tetrahedron Lett. 1980, 21, 221-222;
- (1980) Tetrahedron Lett. , vol.21 , pp. 221-222
- Shanzer, A.¹

41
- 0037051615
- M. J. Martinelli, R. Vaidyanathan, J. M. Pawlak, N. K. Nayyar, U. P. Dhokte, C. W. Doecke, L. M. H. Zollars, E. D. Moher, V. V. Khau, B. Košmrlj, J. Am. Chem. Soc. 2002, 124, 3578-3585;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 3578-3585
- Martinelli, M.J.¹ Vaidyanathan, R.² Pawlak, J.M.³ Nayyar, N.K.⁴ Dhokte, U.P.⁵ Doecke, C.W.⁶ Zollars, L.M.H.⁷ Moher, E.D.⁸ Khau, V.V.⁹ Košmrlj, B.¹⁰

42
- 72149131450
- M. Guillaume, Y. Lang, Tetrahedron Lett. 2010, 51, 579-582;
- (2010) Tetrahedron Lett. , vol.51 , pp. 579-582
- Guillaume, M.¹ Lang, Y.²

43
- 84900489312
- G. Sabitha, K. P. Reddy, S. P. Reddy, J. S. Yadav, Tetrahedron Lett. 2014, 55, 3227.
- (2014) Tetrahedron Lett. , vol.55 , pp. 3227
- Sabitha, G.¹ Reddy, K.P.² Reddy, S.P.³ Yadav, J.S.⁴

44
- 79959531566
- D. Addis, S. Das, K. Junge, M. Beller, Angew. Chem. Int. Ed. 2011, 50, 6004-6011;
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 6004-6011
- Addis, D.¹ Das, S.² Junge, K.³ Beller, M.⁴

45
- 84857012029
- Angew. Chem. 2011, 123, 6128-6135.
- (2011) Angew. Chem. , vol.123 , pp. 6128-6135

46
- 84927922618
- for reviews on frustrated Lewis pair chemistry, see
- M. Oestreich, J. Hermeke, J. Mohr, Chem. Soc. Rev. 2015, 44, 2202-2220; for reviews on frustrated Lewis pair chemistry, see:
- (2015) Chem. Soc. Rev. , vol.44 , pp. 2202-2220
- Oestreich, M.¹ Hermeke, J.² Mohr, J.³

47
- 84923094674
- D. W. Stephan, Acc. Chem. Res. 2015, 48, 306-316;
- (2015) Acc. Chem. Res. , vol.48 , pp. 306-316
- Stephan, D.W.¹

48
- 84903145913
- M. Alcarazo, Synlett 2014, 1519-1520;
- (2014) Synlett , pp. 1519-1520
- Alcarazo, M.¹

49
- 84901838643
- D. W. Stephan, G. Erker, Chem. Sci. 2014, 5, 2625-2641;
- (2014) Chem. Sci. , vol.5 , pp. 2625-2641
- Stephan, D.W.¹ Erker, G.²

50
- 33750866503
- (Eds.: G. Erker, D.W. Stephan), Springer, Berlin
- Topics in Current Chemistry, Vol.332 (Eds.:, G. Erker, D.W. Stephan,), Springer, Berlin, 2013;
- (2013) Topics in Current Chemistry, Vol.332

51
- 33750866503
- (Eds.: G. Erker, D.W. Stephan), Springer, Berlin
- Topics in Current Chemistry, Vol.334 (Eds.:, G. Erker, D.W. Stephan,), Springer, Berlin, 2013;
- (2013) Topics in Current Chemistry, Vol.334

52
- 73349126734
- D. W. Stephan, G. Erker, Angew. Chem. Int. Ed. 2010, 49, 46-76;
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 46-76
- Stephan, D.W.¹ Erker, G.²

53
- 79952598106
- Angew. Chem. 2010, 122, 50-81;
- (2010) Angew. Chem. , vol.122 , pp. 50-81

54
- 80053301509
- W. E. Piers, A. J. V. Marwitz, L. G. Mercier, Inorg. Chem. 2011, 50, 12252-12262.
- (2011) Inorg. Chem. , vol.50 , pp. 12252-12262
- Piers, W.E.¹ Marwitz, A.J.V.² Mercier, L.G.³

55
- 84915779015
- A. Y. Houghton, J. Hurmalainen, A. Mansikkamäki, W. E. Piers, H. M. Tuononen, Nat. Chem. 2014, 6, 983-988;
- (2014) Nat. Chem. , vol.6 , pp. 983-988
- Houghton, A.Y.¹ Hurmalainen, J.² Mansikkamäki, A.³ Piers, W.E.⁴ Tuononen, H.M.⁵

56
- 53549121672
- S. Rendler, M. Oestreich, Angew. Chem. Int. Ed. 2008, 47, 5997-6000;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5997-6000
- Rendler, S.¹ Oestreich, M.²

57
- 62749201739
- Angew. Chem. 2008, 120, 6086-6089.
- (2008) Angew. Chem. , vol.120 , pp. 6086-6089

58
- 0033603612
- 2; see.
- 2; see:, J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers, J. Org. Chem. 1999, 64, 4887-4892.
- (1999) J. Org. Chem. , vol.64 , pp. 4887-4892
- Blackwell, J.M.¹ Foster, K.L.² Beck, V.H.³ Piers, W.E.⁴

59
- 84890231049
- Lithium Aluminium Hydride":, Wiley, Hoboken
- "Lithium Aluminium Hydride": Encyclopedia of Reagents for Organic Synthesis, Wiley, Hoboken, 1999-2014.
- (1999) Encyclopedia of Reagents for Organic Synthesis

60
- 0037155502
- for an example using a cyclohexadiene-derived hydrosilylation reagent, see
- M. Rubin, T. Schwier, V. Gevorgyan, J. Org. Chem. 2002, 67, 1936-1940; for an example using a cyclohexadiene-derived hydrosilylation reagent, see:
- (2002) J. Org. Chem. , vol.67 , pp. 1936-1940
- Rubin, M.¹ Schwier, T.² Gevorgyan, V.³

61
- 84886773605
- A. Simonneau, M. Oestreich, Angew. Chem. Int. Ed. 2013, 52, 11905-11907;
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 11905-11907
- Simonneau, A.¹ Oestreich, M.²

62
- 84897108617
- Angew. Chem. 2013, 125, 12121-12124.
- (2013) Angew. Chem. , vol.125 , pp. 12121-12124

63
- 84887992246
- for a recent example of high enantioselectivities using aliphatic ketones in asymmetric transfer hydrogenation (76-94 % ee), see
- P. Kleman, P. J. Gonzalez-Liste, S. E. García-Garrido, V. Cadierno, A. Pizzano, Chem. Eur. J. 2013, 19, 16209-16212; for a recent example of high enantioselectivities using aliphatic ketones in asymmetric transfer hydrogenation (76-94 % ee), see:
- (2013) Chem. Eur. J. , vol.19 , pp. 16209-16212
- Kleman, P.¹ Gonzalez-Liste, P.J.² García-Garrido, S.E.³ Cadierno, V.⁴ Pizzano, A.⁵

64
- 84869414040
- J. Li, Y. Tang, Q. Wang, X. Li, L. Cun, X. Zhang, J. Zhu, L. Li, J. Deng, J. Am. Chem. Soc. 2012, 134, 18522-18525.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 18522-18525
- Li, J.¹ Tang, Y.² Wang, Q.³ Li, X.⁴ Cun, L.⁵ Zhang, X.⁶ Zhu, J.⁷ Li, L.⁸ Deng, J.⁹

65
- 0142214614
- A. Fürstner, M. Albert, J. Miynarski, M. Matheu, E. DeClercq, J. Am. Chem. Soc. 2003, 125, 13132-13142;
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 13132-13142
- Fürstner, A.¹ Albert, M.² Miynarski, J.³ Matheu, M.⁴ DeClercq, E.⁵

66
- 84863666199
- S.-C. Lin, R.-M. Ho, C.-Y. Chang, C.-S. Hsu, Chem. Eur. J. 2012, 18, 9091-9098.
- (2012) Chem. Eur. J. , vol.18 , pp. 9091-9098
- Lin, S.-C.¹ Ho, R.-M.² Chang, C.-Y.³ Hsu, C.-S.⁴

67
- 84919384159
- X.-H. Yang, K. Wang, S.-F. Zhu, J.-H. Xie, Q.-L. Zhou, J. Am. Chem. Soc. 2014, 136, 17426-17429;
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 17426-17429
- Yang, X.-H.¹ Wang, K.² Zhu, S.-F.³ Xie, J.-H.⁴ Zhou, Q.-L.⁵

68
- 33646844079
- P. Cui, T. L. Macdonald, M. Chen, J. L. Nadler, Bioorg. Med. Chem. Lett. 2006, 16, 3401;
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 3401
- Cui, P.¹ MacDonald, T.L.² Chen, M.³ Nadler, J.L.⁴

69
- 84947872878
- T. L. MacDonald, J. L. Nadler, P. Cui, US20130137693, 2013.
- (2013)
- MacDonald, T.L.¹ Nadler, J.L.² Cui, P.³

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