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Volumn 20, Issue 30, 2014, Pages 9268-9279

Enantioselective construction of quaternary stereogenic carbon atoms by the lewis base catalyzed additions of silyl ketene imines to aldehydes

(3) Denmark, Scott E a Wilson, Tyler W a Burk, Matthew T a

a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN (United States)

Author keywords

aldol reaction; asymmetric synthesis; quaternary stereogenic center; semiempirical calculations; stereoselective catalysis

Indexed keywords

ADDITION REACTIONS; AROMATIC COMPOUNDS; CATALYSIS; CONDENSATION REACTIONS; CYANIDES; ENANTIOSELECTIVITY; KETONES;

ALDOL REACTIONS; ASYMMETRIC SYNTHESIS; SEMI-EMPIRICAL CALCULATION; STEREOGENIC CENTERS; STEREOSELECTIVE CATALYSIS;

ALDEHYDES;

EID: 84904616026 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201403342 Document Type: Article

Times cited : (24)

References (72)

1
- 0001924338
- D. A. Evans, J. V. Nelson, T. R. Taber, Top. Stereochem. 1982, 13, 1-116
- (1982) Top. Stereochem. , vol.13 , pp. 1-116
- Evans, D.A.¹ Nelson, J.V.² Taber, T.R.³

2
- 0000584420
- in (Ed.: J. D. Morrison), Academic Press, New York
- C. H. Heathcock, in Asymmetric Synthesis, Vol. 3 (Ed.:, J. D. Morrison,), Academic Press, New York, 1984, pp. 111-212
- (1984) Asymmetric Synthesis, Vol. 3 , pp. 111-212
- Heathcock, C.H.¹

3
- 0001653533
- in (Ed.: C. H. Heathcock), Pergamon, Oxford
- I. Paterson, in Comprehensive Organic Synthesis Part 2 (Ed.:, C. H. Heathcock,), Pergamon, Oxford, 1991, pp. 301-320
- (1991) Comprehensive Organic Synthesis Part 2 , pp. 301-320
- Paterson, I.¹

4
- 0000922736
- in (Eds.: G. Helmchen, R. Hoffman, J. Mulzer, E. Schaumann), Houben-Weyl, Stuttgart
- M. Braun, in Stereoselective Synthesis Methods of Organic Chemisty, Vol. 3 (Eds.:, G. Helmchen, R. Hoffman, J. Mulzer, E. Schaumann,), Houben-Weyl, Stuttgart, 1996, pp. 1603-1666
- (1996) Stereoselective Synthesis Methods of Organic Chemisty, Vol. 3 , pp. 1603-1666
- Braun, M.¹

5
- 33847093544
- Wiley-VCH, Weinheim, Germany
- R. Mahrwald, Modern Aldol Reactions, Vol. 1 and 2, Wiley-VCH, Weinheim, Germany, 2004
- (2004) Modern Aldol Reactions, Vol. 1 and 2
- Mahrwald, R.¹

6
- 34250900008
- E. M. Carreira, A. Fettes, C. Marti, Org. React. 2006, 67, 1-216.
- (2006) Org. React. , vol.67 , pp. 1-216
- Carreira, E.M.¹ Fettes, A.² Marti, C.³

7
- 0001015795
- E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 2092-2118
- (1998) Angew. Chem. , vol.110 , pp. 2092-2118
- Corey, E.J.¹ Guzman-Perez, A.²

8
- 0032473509
- Angew. Chem. Int. Ed. 1998, 37, 388-401
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 388-401

9
- 0001227615
- J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732
- (2001) Angew. Chem. , vol.113 , pp. 4725-4732
- Christoffers, J.¹ Mann, A.²

10
- 0035905575
- Angew. Chem. Int. Ed. 2001, 40, 4591-4597
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4591-4597

11
- 0344064789
- I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105-10146
- (2003) Tetrahedron , vol.59 , pp. 10105-10146
- Denissova, I.¹ Barriault, L.²

12
- 1842851813
- C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363-5367
- (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 5363-5367
- Douglas, C.J.¹ Overman, L.E.²

13
- 84904614582
- J. Christoffers, A. Baro, Wiley-VCH, Weinheim, Germany, 2005
- J. Christoffers, A. Baro, Wiley-VCH, Weinheim, Germany, 2005

14
- 32644439884
- B. M. Trost, C. Jiang, Synthesis 2006, 369-396
- (2006) Synthesis , pp. 369-396
- Trost, B.M.¹ Jiang, C.²

15
- 67650094837
- M. Bella, T. Gasperi, Synthesis 2009, 1583-1614
- (2009) Synthesis , pp. 1583-1614
- Bella, M.¹ Gasperi, T.²

16
- 77957690100
- C. Hawner, A. Alexakis, Chem. Commun. 2010, 46, 7295-7306.
- (2010) Chem. Commun. , vol.46 , pp. 7295-7306
- Hawner, C.¹ Alexakis, A.²

17
- 34247489350
- I. Marek, G. Sklute, Chem. Commun. 2007, 1683-1691
- (2007) Chem. Commun. , pp. 1683-1691
- Marek, I.¹ Sklute, G.²

18
- 79953694200
- J. P. Das, I. Marek, Chem. Commun. 2011, 47, 4593-4623
- (2011) Chem. Commun. , vol.47 , pp. 4593-4623
- Das, J.P.¹ Marek, I.²

19
- 84894421975
- I. Marek, Y. Minko, M. Pasco, T. Mejuch, N. Gilboa, H. Chechik, J. P. Das, J. Am. Chem. Soc. 2014, 136, 2682-2694.
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 2682-2694
- Marek, I.¹ Minko, Y.² Pasco, M.³ Mejuch, T.⁴ Gilboa, N.⁵ Chechik, H.⁶ Das, J.P.⁷

20
- 4344593453
- E. A. Peterson, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 11943-11948
- (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 11943-11948
- Peterson, E.A.¹ Overman, L.E.²

21
- 84877714252
- A. Y. Hong, B. M. Stoltz, Eur. J. Org. Chem. 2013, 2745-2759.
- (2013) Eur. J. Org. Chem. , pp. 2745-2759
- Hong, A.Y.¹ Stoltz, B.M.²

22
- 33947468884
- H. E. Zimmerman, M. D. Traxler, J. Am. Chem. Soc. 1957, 79, 1920-1923.
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 1920-1923
- Zimmerman, H.E.¹ Traxler, M.D.²

23
- 33847799798
- R. E. Ireland, R. H. Mueller, A. K. Willard, J. Am. Chem. Soc. 1976, 98, 2868-2877.
- (1976) J. Am. Chem. Soc. , vol.98 , pp. 2868-2877
- Ireland, R.E.¹ Mueller, R.H.² Willard, A.K.³

24
- 33847086723
- Z. A. Fataftah, I. E. Kopka, M. W. Rathke, J. Am. Chem. Soc. 1980, 102, 3959-3960
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 3959-3960
- Fataftah, Z.A.¹ Kopka, I.E.² Rathke, M.W.³

25
- 0001113382
- E. J. Corey, A. W. Gross, Tetrahedron Lett. 1984, 25, 495-498
- (1984) Tetrahedron Lett. , vol.25 , pp. 495-498
- Corey, E.J.¹ Gross, A.W.²

26
- 33751499786
- R. E. Ireland, P. Wipf, J. D. Armstrong, J. Org. Chem. 1991, 56, 650-657.
- (1991) J. Org. Chem. , vol.56 , pp. 650-657
- Ireland, R.E.¹ Wipf, P.² Armstrong, J.D.³

27
- 0035819981
- J. M. Manthorpe, J. L. Gleason, J. Am. Chem. Soc. 2001, 123, 2091-2092.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 2091-2092
- Manthorpe, J.M.¹ Gleason, J.L.²

28
- 1342285523
- E. D. Burke, J. L. Gleason, Org. Lett. 2004, 6, 405-407.
- (2004) Org. Lett. , vol.6 , pp. 405-407
- Burke, E.D.¹ Gleason, J.L.²

29
- 65249102908
- E. A. Tiong, J. L. Gleason, Org. Lett. 2009, 11, 1725-1728.
- (2009) Org. Lett. , vol.11 , pp. 1725-1728
- Tiong, E.A.¹ Gleason, J.L.²

30
- 67949106332
- J. P. Das, H. Chechik, I. Marek, Nat. Chem. 2009, 1, 128-132.
- (2009) Nat. Chem. , vol.1 , pp. 128-132
- Das, J.P.¹ Chechik, H.² Marek, I.³

31
- 84867806262
- Y. Minko, M. Pasco, L. Lercher, M. Botoshansky, I. Marek, Nature 2012, 490, 522-526.
- (2012) Nature , vol.490 , pp. 522-526
- Minko, Y.¹ Pasco, M.² Lercher, L.³ Botoshansky, M.⁴ Marek, I.⁵

32
- 84904671867
- C. Allais, A. S. Tsai, P. Nuhant, W. R. Roush, Angew. Chem. 2013, 125, 13126-13129
- (2013) Angew. Chem. , vol.125 , pp. 13126-13129
- Allais, C.¹ Tsai, A.S.² Nuhant, P.³ Roush, W.R.⁴

33
- 84888626647
- Angew. Chem. Int. Ed. 2013, 52, 12888-12891.
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 12888-12891

34
- 53549098253
- D. A. Kummer, W. J. Chain, M. R. Morales, O. Quiroga, A. G. Myers, J. Am. Chem. Soc. 2008, 130, 13231-13233
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 13231-13233
- Kummer, D.A.¹ Chain, W.J.² Morales, M.R.³ Quiroga, O.⁴ Myers, A.G.⁵

35
- 84860765213
- M. R. Morales, K. T. Mellem, A. G. Myers, Angew. Chem. 2012, 124, 4646-4649
- (2012) Angew. Chem. , vol.124 , pp. 4646-4649
- Morales, M.R.¹ Mellem, K.T.² Myers, A.G.³

36
- 84860724488
- Angew. Chem. Int. Ed. 2012, 51, 4568-4571.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4568-4571

37
- 53849121520
- Y.-c. Qin, C. E. Stivala, A. Zakarian, Angew. Chem. 2007, 119, 7610-7613
- (2007) Angew. Chem. , vol.119 , pp. 7610-7613
- Qin, Y.-C.¹ Stivala, C.E.² Zakarian, A.³

38
- 35048820525
- Angew. Chem. Int. Ed. 2007, 46, 7466-7469
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7466-7469

39
- 41149126639
- C. E. Stivala, A. Zakarian, J. Am. Chem. Soc. 2008, 130, 3774-3776.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 3774-3776
- Stivala, C.E.¹ Zakarian, A.²

40
- 6044224571
- N. Mase, F. Tanaka, C. F. Barbas, III, Angew. Chem. 2004, 116, 2474-2477
- (2004) Angew. Chem. , vol.116 , pp. 2474-2477
- Mase, N.¹ Tanaka, F.² Barbas III, C.F.³

41
- 3042625080
- Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2420-2423

42
- 4043170073
- N. S. Chowdari, J. T. Suri, C. F. Barbas, III, Org. Lett. 2004, 6, 2507-2510.
- (2004) Org. Lett. , vol.6 , pp. 2507-2510
- Chowdari, N.S.¹ Suri, J.T.² Barbas III, C.F.³

43
- 0002511331
- R. Kuwano, H. Miyazaki, Y. Ito, J. Organomet. Chem. 2000, 603, 18-29.
- (2000) J. Organomet. Chem. , vol.603 , pp. 18-29
- Kuwano, R.¹ Miyazaki, H.² Ito, Y.³

44
- 23744462875
- A. H. Mermerian, G. C. Fu, Angew. Chem. 2005, 117, 971-974
- (2005) Angew. Chem. , vol.117 , pp. 971-974
- Mermerian, A.H.¹ Fu, G.C.²

45
- 13744263466
- Angew. Chem. Int. Ed. 2005, 44, 949-952
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 949-952

46
- 36849060666
- S. E. Denmark, T. W. Wilson, M. T. Burk, J. R. Heemstra, Jr., J. Am. Chem. Soc. 2007, 129, 14864-14865
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 14864-14865
- Denmark, S.E.¹ Wilson, T.W.² Burk, M.T.³ Heemstra Jr., J.R.⁴

47
- 77953907329
- S. E. Denmark, T. W. Wilson, Synlett 2010, 1723-1728
- (2010) Synlett , pp. 1723-1728
- Denmark, S.E.¹ Wilson, T.W.²

48
- 78049332355
- S. E. Denmark, T. W. Wilson, Nat. Chem. 2010, 2, 937-943
- (2010) Nat. Chem. , vol.2 , pp. 937-943
- Denmark, S.E.¹ Wilson, T.W.²

49
- 79951630465
- G. T. Notte, V. J. M. Baxter, J. L. Leighton, Org. Lett. 2011, 13, 816-818
- (2011) Org. Lett. , vol.13 , pp. 816-818
- Notte, G.T.¹ Baxter, V.J.M.² Leighton, J.L.³

50
- 84866978736
- S. E. Denmark, T. W. Wilson, Angew. Chem. 2012, 124, 3290-3293
- (2012) Angew. Chem. , vol.124 , pp. 3290-3293
- Denmark, S.E.¹ Wilson, T.W.²

51
- 84858754652
- Angew. Chem. Int. Ed. 2012, 51, 3236-3239
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 3236-3239

52
- 84875194851
- S. E. Denmark, T. W. Wilson, Angew. Chem. 2012, 124, 10120-10132
- (2012) Angew. Chem. , vol.124 , pp. 10120-10132
- Denmark, S.E.¹ Wilson, T.W.²

53
- 84867025324
- Angew. Chem. Int. Ed. 2012, 51, 9980-9992
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 9980-9992

54
- 84873640941
- J. Guin, G. Varseev, B. List, J. Am. Chem. Soc. 2013, 135, 2100-2103.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 2100-2103
- Guin, J.¹ Varseev, G.² List, B.³

55
- 15744387149
- S. E. Denmark, G. L. Beutner, T. Wynn, M. D. Eastgate, J. Am. Chem. Soc. 2005, 127, 3774-3789
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 3774-3789
- Denmark, S.E.¹ Beutner, G.L.² Wynn, T.³ Eastgate, M.D.⁴

56
- 45249085012
- S. E. Denmark, W.-j. Chung, J. Org. Chem. 2008, 73, 4582-4595
- (2008) J. Org. Chem. , vol.73 , pp. 4582-4595
- Denmark, S.E.¹ Chung, W.-J.²

57
- 34547130040
- S. E. Denmark, J. R. Heemstra, J. Org. Chem. 2007, 72, 5668-5688.
- (2007) J. Org. Chem. , vol.72 , pp. 5668-5688
- Denmark, S.E.¹ Heemstra, J.R.²

58
- 0001319213
- D. S. Watt, Synth. Commun. 1974, 4, 127-131.
- (1974) Synth. Commun. , vol.4 , pp. 127-131
- Watt, D.S.¹

59
- 84904673737
- CCDC-659734 (39 ad) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.

60
- 38149037245
- S. E. Denmark, B. M. Eklov, Chem. Eur. J. 2008, 14, 234-239
- (2008) Chem. Eur. J. , vol.14 , pp. 234-239
- Denmark, S.E.¹ Eklov, B.M.²

61
- 69049110960
- S. E. Denmark, B. M. Eklov, P. J. Yao, M. D. Eastgate, J. Am. Chem. Soc. 2009, 131, 11770-11787.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 11770-11787
- Denmark, S.E.¹ Eklov, B.M.² Yao, P.J.³ Eastgate, M.D.⁴

62
- 0034832840
- S. E. Denmark, T. Wynn, J. Am. Chem. Soc. 2001, 123, 6199-6200.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6199-6200
- Denmark, S.E.¹ Wynn, T.²

63
- 35448937584
- J. Stewart, J. Mol. Model. 2007, 13, 1173-1213
- (2007) J. Mol. Model. , vol.13 , pp. 1173-1213
- Stewart, J.¹

64
- 0011473607
- Colorado Springs, CO, USA
- J. J. P. Stewart, MOPAC2007 ed., Stewart Computational Chemistry, Colorado Springs, CO, USA, http://OpenMOPAC.net, 2007.
- (2007) MOPAC2007 Ed., Stewart Computational Chemistry
- Stewart, J.J.P.¹

65
- 33845373936
- C. H. Heathcock, S. K. Davidsen, K. T. Hug, L. A. Flippin, J. Org. Chem. 1986, 51, 3027-3037
- (1986) J. Org. Chem. , vol.51 , pp. 3027-3037
- Heathcock, C.H.¹ Davidsen, S.K.² Hug, K.T.³ Flippin, L.A.⁴

66
- 0001180683
- S. E. Denmark, B. R. Henke, J. Am. Chem. Soc. 1989, 111, 8032-8034
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8032-8034
- Denmark, S.E.¹ Henke, B.R.²

67
- 0001672799
- S. E. Denmark, B. D. Griedel, D. M. Coe, J. Org. Chem. 1993, 58, 988-990
- (1993) J. Org. Chem. , vol.58 , pp. 988-990
- Denmark, S.E.¹ Griedel, B.D.² Coe, D.M.³

68
- 0001432032
- S. E. Denmark, B. R. Henke, J. Am. Chem. Soc. 1991, 113, 2177-2194.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 2177-2194
- Denmark, S.E.¹ Henke, B.R.²

69
- 54849441320
- S. E. Denmark, W. Lee, Chem. Asian J. 2008, 3, 327-341.
- (2008) Chem. Asian J. , vol.3 , pp. 327-341
- Denmark, S.E.¹ Lee, W.²

70
- 0001337104
- J. C. Jochims, J. Lambrecht, U. Burkert, L. Zsolnai, G. Huttner, Tetrahedron 1984, 40, 893-903
- (1984) Tetrahedron , vol.40 , pp. 893-903
- Jochims, J.C.¹ Lambrecht, J.² Burkert, U.³ Zsolnai, L.⁴ Huttner, G.⁵

71
- 84982071614
- J. Lambrecht, B. Gambke, J. Vonseyerl, G. Huttner, G. K. Nell, S. Herzberger, J. C. Jochims, Chem. Ber. 1981, 114, 3751-3771.
- (1981) Chem. Ber. , vol.114 , pp. 3751-3771
- Lambrecht, J.¹ Gambke, B.² Vonseyerl, J.³ Huttner, G.⁴ Nell, G.K.⁵ Herzberger, S.⁶ Jochims, J.C.⁷

72
- 0033575491
- S. E. Denmark, X. P. Su, Tetrahedron 1999, 55, 8727-8738.
- (1999) Tetrahedron , vol.55 , pp. 8727-8738
- Denmark, S.E.¹ Su, X.P.²

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