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Synlett

Volumn , Issue 15, 2007, Pages 2448-2450

Enantioselective cyanoformylation of aldehydes catalyzed by a chiral quaternary ammonium salt and triethylamine

(6) Peng, Dan a Zhou, Hui a Liu, Xiaohua a Wang, Liwei a Chen, Shikui a Feng, Xiaoming a

a SICHUAN UNIVERSITY (China)

Author keywords

Aldehyde; Cyanation; Ethyl cyanoformate; Organocatalysis; Quaternary ammonium salt

Indexed keywords

ALDEHYDE; AMMONIUM DERIVATIVE; TRIETHYLAMINE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TEMPERATURE DEPENDENCE;

EID: 34948878544 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-986625 Document Type: Article

Times cited : (33)

References (48)

1
- 19644385319
- For reviews on the synthesis and applications of cyanohydrins, see: a, Murahashi, S. I, Ed, Thieme: Stuttgart
- For reviews on the synthesis and applications of cyanohydrins, see: (a) North, M. Science of Synthesis, Vol. 19; Murahashi, S. I., Ed.; Thieme: Stuttgart, 2004, 235-284.
- (2004) Science of Synthesis , vol.19 , pp. 235-284
- North, M.¹

2
- 0036402658
- (b) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989.
- (1989) Chem. Commun , vol.2002
- Shibasaki, M.¹ Kanai, M.² Funabashi, K.³

3
- 0003412412
- 5th ed, John Wiley & Sons: New York
- (c) Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; John Wiley & Sons: New York, 2001, 1239-1240.
- (2001) Advanced Organic Chemistry , pp. 1239-1240
- Smith, M.B.¹ March, J.²

4
- 84891580093
- John Wiley & Sons: Chichester
- (d) Ojima, I. Catalytic Asymmetric Synthesis; John Wiley & Sons: Chichester, 2000, 235-284.
- (2000) Catalytic Asymmetric Synthesis , pp. 235-284
- Ojima, I.¹

5
- 0000140586
- (e) Gregory, R. J. H. Chem. Rev. 1999, 99, 3649.
- (1999) Chem. Rev , vol.99 , pp. 3649
- Gregory, R.J.H.¹

6
- 0001678717
- Cyanation of Carbonyl and Amino Groups
- Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer-Verlag: Heidelberg
- (f) Mori, A.; Inoue, S. Cyanation of Carbonyl and Amino Groups, In Comprehensive Asymmetric Synthesis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999, 983-992.
- (1999) Comprehensive Asymmetric Synthesis , pp. 983-992
- Mori, A.¹ Inoue, S.²

7
- 33748215202
- (g) Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555.
- (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 1555
- Effenberger, F.¹

8
- 33746233274
- For recent reviews on cyanation reactions, see: a
- For recent reviews on cyanation reactions, see: (a) Chen, F. X.; Feng, X. M. Curr. Org. Synth. 2006, 3, 77.
- (2006) Curr. Org. Synth , vol.3 , pp. 77
- Chen, F.X.¹ Feng, X.M.²

9
- 34948817477
- (b) Thierry, R. J. A.; Clutterbuck, L. A.; Michael, N. Synlett 2005, 1828.
- (2005) Synlett , pp. 1828
- Thierry, R.J.A.¹ Clutterbuck, L.A.² Michael, N.³

10
- 21544444468
- (c) Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491.
- (2005) Synlett , pp. 1491
- Kanai, M.¹ Kato, N.² Ichikawa, E.³ Shibasaki, M.⁴

11
- 17144385820
- (d) Chen, F. X.; Feng, X. M. Synlett 2005, 892.
- (2005) Synlett , pp. 892
- Chen, F.X.¹ Feng, X.M.²

12
- 3242810683
- (e) Brunei, J. M.; Holmes, I. P. Angew. Chem. Int. Ed. 2004, 43, 2752.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 2752
- Brunei, J.M.¹ Holmes, I.P.²

13
- 0037449629
- (f) North, M. Tetrahedron: Asymmetry 2003, 14, 147.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 147
- North, M.¹

14
- 33645966549
- (a) Xiong, Y.; Huang, X.; Gou, S. H.; Huang, J. L.; Wen, Y. H.; Feng, X. M. Adv. Synth. Catal. 2006, 348, 538.
- (2006) Adv. Synth. Catal , vol.348 , pp. 538
- Xiong, Y.¹ Huang, X.² Gou, S.H.³ Huang, J.L.⁴ Wen, Y.H.⁵ Feng, X.M.⁶

15
- 24644518441
- (b) Liu, X. H.; Qin, B.; Zhou, X.; He, B.; Feng, X. M. J. Am. Chem. Soc. 2005, 127, 12224.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 12224
- Liu, X.H.¹ Qin, B.² Zhou, X.³ He, B.⁴ Feng, X.M.⁵

16
- 17644414916
- (c) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 5384
- Ryu, D.H.¹ Corey, E.J.²

17
- 21244472590
- (d) Fuerst, D. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 8964.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 8964
- Fuerst, D.E.¹ Jacobsen, E.N.²

18
- 26844570657
- (e) Wen, Y. H.; Huang, X.; Huang, J. L.; Xiong, Y.; Qin, B.; Feng, X. M. Synlett 2005, 2445.
- (2005) Synlett , pp. 2445
- Wen, Y.H.¹ Huang, X.² Huang, J.L.³ Xiong, Y.⁴ Qin, B.⁵ Feng, X.M.⁶

19
- 20544468477
- (f) Qin, Y. C.; Liu, L.; Pu, L. Org. Lett. 2005, 7, 2381.
- (2005) Org. Lett , vol.7 , pp. 2381
- Qin, Y.C.¹ Liu, L.² Pu, L.³

20
- 8644289262
- (g) Li, Y.; He, B.; Qin, B.; Feng, X. M.; Zhang, G. L. J. Org. Chem. 2004, 69, 7910.
- (2004) J. Org. Chem , vol.69 , pp. 7910
- Li, Y.¹ He, B.² Qin, B.³ Feng, X.M.⁴ Zhang, G.L.⁵

21
- 0042522434
- (h) Tian, S. K.; Hong, R.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 9900
- Tian, S.K.¹ Hong, R.² Deng, L.³

22
- 0034833715
- (a) Tian, S. K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 6195
- Tian, S.K.¹ Deng, L.²

23
- 33750441834
- (b) Tian, S. K.; Deng, L. Tetrahedron 2006, 62, 11320.
- (2006) Tetrahedron , vol.62 , pp. 11320
- Tian, S.K.¹ Deng, L.²

24
- 14944386585
- (a) Yamagiwa, N.; Tian, J.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 3413.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 3413
- Yamagiwa, N.¹ Tian, J.² Matsunaga, S.³ Shibasaki, M.⁴

25
- 0141744527
- (b) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2003, 5, 3021.
- (2003) Org. Lett , vol.5 , pp. 3021
- Tian, J.¹ Yamagiwa, N.² Matsunaga, S.³ Shibasaki, M.⁴

26
- 0037020417
- (c) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem. Int. Ed. 2002, 41, 3636.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 3636
- Tian, J.¹ Yamagiwa, N.² Matsunaga, S.³ Shibasaki, M.⁴

27
- 33646198861
- (a) Baeza, A.; Casas, J.; Nájera, C.; Sansano, J. M.; Saá, J. M. Eur. J. Org. Chem. 2006, 71, 1949.
- (2006) Eur. J. Org. Chem , vol.71 , pp. 1949
- Baeza, A.¹ Casas, J.² Nájera, C.³ Sansano, J.M.⁴ Saá, J.M.⁵

28
- 23044482263
- (b) Baeza, A.; Nájera, C.; Sansano, J. M.; Saá, J. M. Tetrahedron: Asymmetry 2005, 16, 2385.
- (2005) Tetrahedron: Asymmetry , vol.16 , pp. 2385
- Baeza, A.¹ Nájera, C.² Sansano, J.M.³ Saá, J.M.⁴

29
- 0037449604
- (c) Casas, J.; Baeza, A.; Sansano, J. M.; Nájera, C.; Saá, J. M. Tetrahedron: Asymmetry 2003, 14, 197.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 197
- Casas, J.¹ Baeza, A.² Sansano, J.M.³ Nájera, C.⁴ Saá, J.M.⁵

30
- 0042812083
- (d) Baeza, A.; Casas, J.; Nájera, C.; Sansano, J. M.; Saá, J. M. Angew. Chem. Int. Ed. 2003, 42, 3143.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 3143
- Baeza, A.¹ Casas, J.² Nájera, C.³ Sansano, J.M.⁴ Saá, J.M.⁵

31
- 5044235082
- (a) Belokon, Y. N.; Blacker, A. J.; Carta, P.; Clutterbuck, L. A.; North, M. Tetrahedron 2004, 60, 10433.
- (2004) Tetrahedron , vol.60 , pp. 10433
- Belokon, Y.N.¹ Blacker, A.J.² Carta, P.³ Clutterbuck, L.A.⁴ North, M.⁵

32
- 0344496716
- (b) Belokon, Y. N.; Blacker, A. J.; Clutterbuck, L. A.; North, M. Org. Lett. 2003, 5, 4505.
- (2003) Org. Lett , vol.5 , pp. 4505
- Belokon, Y.N.¹ Blacker, A.J.² Clutterbuck, L.A.³ North, M.⁴

33
- 23944488799
- Lundgren, S.; Wingstrand, E.; Penhoat, M.; Moberg, C. J. Am. Chem. Soc. 2005, 127, 11592.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 11592
- Lundgren, S.¹ Wingstrand, E.² Penhoat, M.³ Moberg, C.⁴

34
- 33846603744
- (a) Chen, S. K.; Peng, D.; Zhou, H.; Wang, L. W.; Chen, F. X.; Feng, X. M. Eur. J. Org. Chem. 2007, 639.
- (2007) Eur. J. Org. Chem , pp. 639
- Chen, S.K.¹ Peng, D.² Zhou, H.³ Wang, L.W.⁴ Chen, F.X.⁵ Feng, X.M.⁶

35
- 33947580322
- (b) Gou, S. H.; Wang, J.; Liu, X. H.; Wang, W. T.; Chen, F. X.; Feng, X. M. Adv. Synth. Catal. 2007, 349, 343.
- (2007) Adv. Synth. Catal , vol.349 , pp. 343
- Gou, S.H.¹ Wang, J.² Liu, X.H.³ Wang, W.T.⁴ Chen, F.X.⁵ Feng, X.M.⁶

36
- 33746355281
- (c) Gou, S. H.; Chen, X. H.; Xiong, Y.; Feng, X. M. J. Org. Chem. 2006, 71, 5732.
- (2006) J. Org. Chem , vol.71 , pp. 5732
- Gou, S.H.¹ Chen, X.H.² Xiong, Y.³ Feng, X.M.⁴

37
- 33746292422
- (d) Li, Q. H.; Chang, L.; Liu, X. H.; Feng, X. M. Synlett 2006, 1675.
- (2006) Synlett , pp. 1675
- Li, Q.H.¹ Chang, L.² Liu, X.H.³ Feng, X.M.⁴

38
- 0348225177
- For a chemoenzymatic one-pot reaction of ethyl cyanoformate with benzaldehyde catalyzed by hydroxynitrile lyase, see: Purkarthofer, T, Skranc, W, Weber, H, Griengl, H, Wubbolts, M, Scholz, G, Pöchlauer, P. Tetrahedron 2004, 60, 735
- For a chemoenzymatic one-pot reaction of ethyl cyanoformate with benzaldehyde catalyzed by hydroxynitrile lyase, see: Purkarthofer, T.; Skranc, W.; Weber, H.; Griengl, H.; Wubbolts, M.; Scholz, G.; Pöchlauer, P. Tetrahedron 2004, 60, 735.

39
- 3142749638
- Zhou, H.; Chen, F. X.; Qin, B.; Feng, X. M.; Zhang, G. L. Synlett 2004, 1077.
- (2004) Synlett , pp. 1077
- Zhou, H.¹ Chen, F.X.² Qin, B.³ Feng, X.M.⁴ Zhang, G.L.⁵

40
- 34948897823
- Procedure for Preparation of 2h: To a solution of 2g (0.100 g, 0.158 mmol) in CH2Cl2 (10 mL) at r.t. was added MeCOOAg (0.0277 g, 0.166 mmol, 1.05 equiv, and the mixture was stirred in the dark at r.t. for one week. The residue was centrifuged for half an hour. Then the precipitate was filtered off and the filtrate was concentrated under reduced pressure to afford a yellow solid; mp 142-143°C; [α]D 25 121 (c, 0.108, CHCl3, IR (KBr, 3411, 2931, 2361, 1622, 1509, 1374, 1280, 1178, 1136, 905, 683 cm-1. 1H NMR (300 MHz, CDCl3, δ, 8.57 (d, J, 4.5 Hz, 1 H, 8.02 (s, 1 H, 7.66-7.81 (m, 4 H, 7.24-7.25 (m, 1 H, 6.94-6.98 (dd, J, 2.3, 9.2 Hz, 1 H, 6.49 (d, J, 12.5 Hz, 1 H, 6.37 (s, 1 H, 5.82-5.94 (sept, 1 H, 5.41 (d, J, 13.1 Hz, 1 H, 5.17-5.25 (m, 1 H, 4.70 (t, J, 10.5 Hz, 1 H, 4.52 t, J, 10.1 Hz, 1 H, 4.15
- 2: 551.2128; found: 551.2020.

41
- 3843123354
- Ohshima, T.; Shibuguchi, T.; Fukuta, Y.; Shibasaki, M. Tetrahedron 2004, 60, 7743.
- (2004) Tetrahedron , vol.60 , pp. 7743
- Ohshima, T.¹ Shibuguchi, T.² Fukuta, Y.³ Shibasaki, M.⁴

42
- 34948897314
- Typical Procedure: To a mixture of benzaldehyde (0.1 mmol, quaternary ammonium salt 2h (0.01 mmol, 10 mol, and Et3N (0.01 mmol) in CH2Cl2 (2 mL) under a N2 atmosphere, was added ethyl cyanoformate (0.15 mmol, 1.5 equiv) at -78°C. The reaction was monitored by TLC, and after the reaction time indicated in Table 3, the residue was directly purified by silica gel column chromatography (PE-Et2O, 10:1) to afford the title compound as a colorless oil in 96% yield with 67% ee as determined by HPLC analysis with a Chiralcel OD-H column [λ, 254 nm, hexane-2-propanol, 99:1, 1.0 mL/min, t R(major, 9.2 min, tR(minor, 10.9 min, α]D25, 6.49 (c, 0.154, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 7.53-7.56 (m, 2 H, ArH, 745-7.49 (m, 3 H, ArH, 6.27 (s, 1 H, OCHCN, 4.26-4.32 m, 2 H, OCH 2, 1.34
- 3).

43
- 34948838695
- Only 50% ee was obtained for the corresponding product of cyclohexanal and isopropanal
- Only 50% ee was obtained for the corresponding product of cyclohexanal and isopropanal.

44
- 0034699310
- (a) Perrard, T.; Plaquevent, J.; Desmurs, J.; Hébrault, D. Org. Lett. 2000, 2, 2959.
- (2000) Org. Lett , vol.2 , pp. 2959
- Perrard, T.¹ Plaquevent, J.² Desmurs, J.³ Hébrault, D.⁴

45
- 29344438414
- (b) Palomo, C.; Oiarbide, M.; Laso, A.; López, R. J. Am. Chem. Soc. 2005, 127, 17622.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 17622
- Palomo, C.¹ Oiarbide, M.² Laso, A.³ López, R.⁴

46
- 0025118618
- (c) Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265.
- (1990) Tetrahedron: Asymmetry , vol.1 , pp. 265
- Nerinckx, W.¹ Vandewalle, M.²

47
- 3042815030
- (d) Ooi, T.; Ohara, D.; Tamura, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 6844.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 6844
- Ooi, T.¹ Ohara, D.² Tamura, M.³ Maruoka, K.⁴

48
- 23044474944
- (e) Ooi, T.; Ohara, D.; Fukumoto, K.; Maruoka, K. Org. Lett. 2005, 7, 3195.
- (2005) Org. Lett , vol.7 , pp. 3195
- Ooi, T.¹ Ohara, D.² Fukumoto, K.³ Maruoka, K.⁴

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