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Angewandte Chemie - International Edition

Volumn 51, Issue 38, 2012, Pages 9539-9542

Observation of a transient intermediate in Soai's asymmetric autocatalysis: Insights from 1H NMR turnover in real time

(5) Gehring, Timo a Quaranta, Michela b Odell, Barbara a Blackmond, Donna G c Brown, John M a

a UNIVERSITY OF OXFORD (United Kingdom)

b IMPERIAL COLLEGE LONDON (United Kingdom)

c SCRIPPS RESEARCH INSTITUTE (United States)

Author keywords

asymmetric catalysis; autocatalysis; NMR spectroscopy; Soai reaction; zinc

Indexed keywords

ALKOXIDES; ASYMMETRIC CATALYSIS; AUTOCATALYSIS; H NMR SPECTROSCOPY; REAL TIME; SOAI REACTION; TRANSIENT INTERMEDIATE;

ALDEHYDES; ZINC;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALDEHYDE; ORGANOMETALLIC COMPOUND; PROTON; ZINC;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TIME;

ALDEHYDES; ALKYLATION; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLIC COMPOUNDS; PROTONS; TIME FACTORS; ZINC;

EID: 84866411010 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201203398 Document Type: Article

Times cited : (79)

References (51)

1
- 0029559848
- K. Soai, T. Shibata, H. Morioka, K. Choji, Nature 1995, 378, 767-768.
- (1995) Nature , vol.378 , pp. 767-768
- Soai, K.¹ Shibata, T.² Morioka, H.³ Choji, K.⁴

2
- 0005540903
- Asymmetric autocatalytic amplification, as a model for the origins of chirality in biology, had been mooted many years before.
- Asymmetric autocatalytic amplification, as a model for the origins of chirality in biology, had been mooted many years before:, F. C. Frank, Biochim. Biophys. Acta 1953, 11, 459-463.
- (1953) Biochim. Biophys. Acta , vol.11 , pp. 459-463
- Frank, F.C.¹

3
- 78349278412
- EE 182
- T. Gehring, M. Busch, M. Schlageter, D. Weingand, Chirality 2010, 22, E 173 -E 182
- (2010) Chirality , vol.22 , pp. 173
- Gehring, T.¹ Busch, M.² Schlageter, M.³ Weingand, D.⁴

4
- 77949491132
- T. Kawasaki, K. Soai, J. Fluorine Chem. 2010, 131, 525-534
- (2010) J. Fluorine Chem. , vol.131 , pp. 525-534
- Kawasaki, T.¹ Soai, K.²

5
- 61349166211
- K. Soai, T. Kawasaki, Top. Curr. Chem. 2008, 284, 1-33
- (2008) Top. Curr. Chem. , vol.284 , pp. 1-33
- Soai, K.¹ Kawasaki, T.²

6
- 33646441370
- I. D. Gridnev, Chem. Lett. 2006, 35, 148-153.
- (2006) Chem. Lett. , vol.35 , pp. 148-153
- Gridnev, I.D.¹

7
- 0030602193
- T. Shibata, H. Morioka, S. Tanji, T. Hayase, Y. Kodaka, K. Soai, Tetrahedron Lett. 1996, 37, 8783-8786
- (1996) Tetrahedron Lett. , vol.37 , pp. 8783-8786
- Shibata, T.¹ Morioka, H.² Tanji, S.³ Hayase, T.⁴ Kodaka, Y.⁵ Soai, K.⁶

8
- 0029967849
- T. Shibata, K. Choji, H. Morioka, T. Hayase, K. Soai, Chem. Commun. 1996, 751-752.
- (1996) Chem. Commun. , pp. 751-752
- Shibata, T.¹ Choji, K.² Morioka, H.³ Hayase, T.⁴ Soai, K.⁵

9
- 0037449649
- K. Soai, I. Sato, T. Shibata, S. Komiya, M. Hayashi, Y. Matsueda, H. Imamura, T. Hayase, H. Morioka, H. Tabira, J. Yamamoto, Y. Kowata, Tetrahedron: Asymmetry 2003, 14, 185-188
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 185-188
- Soai, K.¹ Sato, I.² Shibata, T.³ Komiya, S.⁴ Hayashi, M.⁵ Matsueda, Y.⁶ Imamura, H.⁷ Hayase, T.⁸ Morioka, H.⁹ Tabira, H.¹⁰ Yamamoto, J.¹¹ Kowata, Y.¹²

10
- 0344981496
- I. D. Gridnev, J. M. Serafimov, H. Quiney, J. M. Brown, Org. Biomol. Chem. 2003, 1, 3811-3819
- (2003) Org. Biomol. Chem. , vol.1 , pp. 3811-3819
- Gridnev, I.D.¹ Serafimov, J.M.² Quiney, H.³ Brown, J.M.⁴

11
- 0345359342
- D. A. Singleton, L. K. Vo, Org. Lett. 2003, 5, 4337-4339.
- (2003) Org. Lett. , vol.5 , pp. 4337-4339
- Singleton, D.A.¹ Vo, L.K.²

12
- 0001592561
- B. L. Feringa, D. R. A. van Delden, Angew. Chem. 1999, 111, 3624-3645
- (1999) Angew. Chem. , vol.111 , pp. 3624-3645
- Feringa, B.L.¹ Van Delden, D.R.A.²

13
- 0033521221
- Angew. Chem. Int. Ed. 1999, 38, 3418-3438
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3418-3438

14
- 0038044642
- K. Mislow, Collect. Czech. Chem. Commun. 2003, 68, 849-864.
- (2003) Collect. Czech. Chem. Commun. , vol.68 , pp. 849-864
- Mislow, K.¹

15
- 4544254566
- I. Sato, H. Urabe, S. Ishiguro, T. Shibata, K. Soai, Angew. Chem. 2003, 115, 329-331
- (2003) Angew. Chem. , vol.115 , pp. 329-331
- Sato, I.¹ Urabe, H.² Ishiguro, S.³ Shibata, T.⁴ Soai, K.⁵

16
- 0037455228
- Angew. Chem. Int. Ed. 2003, 42, 315-317.
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 315-317

17
- 79951875099
- T. Kawasaki, H. Ozawa, M. Ito, K. Soai, Chem. Lett. 2011, 40, 320-321
- (2011) Chem. Lett. , vol.40 , pp. 320-321
- Kawasaki, T.¹ Ozawa, H.² Ito, M.³ Soai, K.⁴

18
- 84866410637
- T. Kawasaki, S. Kamimura, A. Amihara, K. Suzuki, K. Soai, Angew. Chem. 2011, 123, 6928-6930
- (2011) Angew. Chem. , vol.123 , pp. 6928-6930
- Kawasaki, T.¹ Kamimura, S.² Amihara, A.³ Suzuki, K.⁴ Soai, K.⁵

19
- 79960252490
- Angew. Chem. Int. Ed. 2011, 50, 6796-6798
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 6796-6798

20
- 79955583986
- T. Kawasaki, T. Sasagawa, K. Shiozawa, M. Uchida, K. Suzuki, K. Soai, Org. Lett. 2011, 13, 2361-2363
- (2011) Org. Lett. , vol.13 , pp. 2361-2363
- Kawasaki, T.¹ Sasagawa, T.² Shiozawa, K.³ Uchida, M.⁴ Suzuki, K.⁵ Soai, K.⁶

21
- 77949344389
- T. Kawasaki, M. Nakaoda, N. Kaito, T. Sasagawa, K. Soai, Origins Life Evol. Biosphere 2010, 40, 65-78
- (2010) Origins Life Evol. Biosphere , vol.40 , pp. 65-78
- Kawasaki, T.¹ Nakaoda, M.² Kaito, N.³ Sasagawa, T.⁴ Soai, K.⁵

22
- 77950372660
- T. Kawasaki, Y. Hakoda, H. Mineki, K. Suzuki, K. Soai, J. Am. Chem. Soc. 2010, 132, 2874-2875.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 2874-2875
- Kawasaki, T.¹ Hakoda, Y.² Mineki, H.³ Suzuki, K.⁴ Soai, K.⁵

23
- 65449159829
- 13C
- 13C:, T. Kawasaki, Y. Matsumura, T. Tsutsumi, K. Suzuki, M. Ito, K. Soai, Science 2009, 324, 492-495
- (2009) Science , vol.324 , pp. 492-495
- Kawasaki, T.¹ Matsumura, Y.² Tsutsumi, T.³ Suzuki, K.⁴ Ito, M.⁵ Soai, K.⁶

24
- 84873983674
- 18O
- 18O:, T. Kawasaki, Y. Okano, E. Suzuki, S. Takano, S. Oji, K. Soai, Angew. Chem. 2011, 123, 8281-8283
- (2011) Angew. Chem. , vol.123 , pp. 8281-8283
- Kawasaki, T.¹ Okano, Y.² Suzuki, E.³ Takano, S.⁴ Oji, S.⁵ Soai, K.⁶

25
- 80051767177
- Angew. Chem. Int. Ed. 2011, 50, 8131-8133
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 8131-8133

26
- 0035904413
- D. G. Blackmond, C. R. McMillan, S. Ramdeehul, A. Schorm, J. M. Brown, J. Am. Chem. Soc. 2001, 123, 10103-10104.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 10103-10104
- Blackmond, D.G.¹ McMillan, C.R.² Ramdeehul, S.³ Schorm, A.⁴ Brown, J.M.⁵

27
- 0043261499
- F. G. Buono, D. G. Blackmond, J. Am. Chem. Soc. 2003, 125, 8978-8979.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 8978-8979
- Buono, F.G.¹ Blackmond, D.G.²

28
- 18844419251
- I. D. Gridnev, J. M. Serafimov, J. M. Brown, Angew. Chem. 2004, 116, 4992-4995
- (2004) Angew. Chem. , vol.116 , pp. 4992-4995
- Gridnev, I.D.¹ Serafimov, J.M.² Brown, J.M.³

29
- 4744354453
- Angew. Chem. Int. Ed. 2004, 43, 4884-4887.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4884-4887

30
- 68949088978
- L. Schiaffino, G. Ercolani, Angew. Chem. 2008, 120, 6938-6941
- (2008) Angew. Chem. , vol.120 , pp. 6938-6941
- Schiaffino, L.¹ Ercolani, G.²

31
- 53249103664
- Angew. Chem. Int. Ed. 2008, 47, 6832-6835
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6832-6835

32
- 70349775663
- L. Schiaffino, G. Ercolani, ChemPhysChem 2009, 10, 2508-2515
- (2009) ChemPhysChem , vol.10 , pp. 2508-2515
- Schiaffino, L.¹ Ercolani, G.²

33
- 77649204528
- L. Schiaffino, G. Ercolani, Chem. Eur. J. 2010, 16, 3147-3156
- (2010) Chem. Eur. J. , vol.16 , pp. 3147-3156
- Schiaffino, L.¹ Ercolani, G.²

34
- 79953888346
- G. Ercolani, L. Schiaffino, J. Org. Chem. 2011, 76, 2619-2626.
- (2011) J. Org. Chem. , vol.76 , pp. 2619-2626
- Ercolani, G.¹ Schiaffino, L.²

35
- 68949101681
- M. Busch, M. Schlageter, D. Weingand, T. Gehring, Chem. Eur. J. 2009, 15, 8251-8258.
- (2009) Chem. Eur. J. , vol.15 , pp. 8251-8258
- Busch, M.¹ Schlageter, M.² Weingand, D.³ Gehring, T.⁴

36
- 78049379812
- M. Quaranta, T. Gehring, B. Odell, J. M. Brown, D. G. Blackmond, J. Am. Chem. Soc. 2010, 132, 15104-15107.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 15104-15107
- Quaranta, M.¹ Gehring, T.² Odell, B.³ Brown, J.M.⁴ Blackmond, D.G.⁵

37
- 34547462586
- J. Klankermayer, I. D. Gridnev, J. M. Brown, Chem. Commun. 2007, 3151-3153.
- (2007) Chem. Commun. , pp. 3151-3153
- Klankermayer, J.¹ Gridnev, I.D.² Brown, J.M.³

38
- 49649151525
- earlier papers
- M. Anteunis, G. Swaelens, J. Gelan, Tetrahedron 1971, 27, 1917-1929, and earlier papers
- (1971) Tetrahedron , vol.27 , pp. 1917-1929
- Anteunis, M.¹ Swaelens, G.² Gelan, J.³

39
- 10944237213
- W. Migda, B. Rys, Magn. Reson. Chem. 2004, 42, 459-466.
- (2004) Magn. Reson. Chem. , vol.42 , pp. 459-466
- Migda, W.¹ Rys, B.²

40
- 33751391942
- M. Watanabe, N. Hashimoto, S. Araki, Y. Butsugan, J. Org. Chem. 1992, 57, 742-744
- (1992) J. Org. Chem. , vol.57 , pp. 742-744
- Watanabe, M.¹ Hashimoto, N.² Araki, S.³ Butsugan, Y.⁴

41
- 0030583528
- K. Soai, Y. Inoue, T. Takahashi, T. Shibata, Tetrahedron 1996, 52, 13355-13362
- (1996) Tetrahedron , vol.52 , pp. 13355-13362
- Soai, K.¹ Inoue, Y.² Takahashi, T.³ Shibata, T.⁴

42
- 0035806295
- H. Kleijn, J. T. B. H. Jastrzebski, J. Boersma, G. van Koten, Tetrahedron Lett. 2001, 42, 3933-3937.
- (2001) Tetrahedron Lett. , vol.42 , pp. 3933-3937
- Kleijn, H.¹ Jastrzebski, J.T.B.H.² Boersma, J.³ Van Koten, G.⁴

43
- 20544441249
- K. Asakawa, J. J. Dannenberg, K. J. Fitch, S. S. Hall, C. Kadowaki, S. Karady, S. Kii, K. Maeda, B. F. Marcune, T. Mase, R. A. Miller, R. A. Reamer, D. M. Tschaen, Tetrahedron Lett. 2005, 46, 5081-5084
- (2005) Tetrahedron Lett. , vol.46 , pp. 5081-5084
- Asakawa, K.¹ Dannenberg, J.J.² Fitch, K.J.³ Hall, S.S.⁴ Kadowaki, C.⁵ Karady, S.⁶ Kii, S.⁷ Maeda, K.⁸ Marcune, B.F.⁹ Mase, T.¹⁰ Miller, R.A.¹¹ Reamer, R.A.¹² Tschaen, D.M.¹³

44
- 0037121778
- A. Avenoza, J. H. Busto, J. M. Peregrina, Tetrahedron 2002, 58, 10167-10171.
- (2002) Tetrahedron , vol.58 , pp. 10167-10171
- Avenoza, A.¹ Busto, J.H.² Peregrina, J.M.³

45
- 33646444491
- L. O. Müller, R. Scopelliti, I. Krossing, Chimia 2006, 60, 220-223.
- (2006) Chimia , vol.60 , pp. 220-223
- Müller, L.O.¹ Scopelliti, R.² Krossing, I.³

46
- 12344286314
- K. E. Price, S. J. Broadwater, H. M. Jung, D. T. McQuade, Org. Lett. 2005, 7, 147-150
- (2005) Org. Lett. , vol.7 , pp. 147-150
- Price, K.E.¹ Broadwater, S.J.² Jung, H.M.³ McQuade, D.T.⁴

47
- 18744378020
- K. E. Price, S. J. Broadwater, B. J. Walker, D. T. McQuade, J. Org. Chem. 2005, 70, 3980-3987
- (2005) J. Org. Chem. , vol.70 , pp. 3980-3987
- Price, K.E.¹ Broadwater, S.J.² Walker, B.J.³ McQuade, D.T.⁴

48
- 37849014325
- R. Robiette, V. K. Aggarwal, J. N. Harvey, J. Am. Chem. Soc. 2007, 129, 15513-15525.
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 15513-15525
- Robiette, R.¹ Aggarwal, V.K.² Harvey, J.N.³

49
- 70450206724
- Rev C.1, Gaussian, Inc., Wallingford CT, 2009; see Supporting Information for full details
- Gaussian 09; Rev C.1: M. J. Frisch et al., Gaussian, Inc., Wallingford CT, 2009; see Supporting Information for full details.
- Gaussian 09
- Frisch, M.J.¹

50
- 0034604501
- A. Boudier, C. Darcel, F. Flachsmann, L. Micouin, M. Oestreich, P. Knochel, Chem. Eur. J. 2000, 6, 2748-2753.
- (2000) Chem. Eur. J. , vol.6 , pp. 2748-2753
- Boudier, A.¹ Darcel, C.² Flachsmann, F.³ Micouin, L.⁴ Oestreich, M.⁵ Knochel, P.⁶

51
- 33644924126
- A. Krasovshiy, P. Knochel, Synthesis 2006, 890-891.
- (2006) Synthesis , pp. 890-891
- Krasovshiy, A.¹ Knochel, P.²

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