SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 4, 2008, Pages 555-560

Catalytic enantioselective Mukaiyama-Michael reaction of 2-(trimethylsilyloxy)furan with α′-phenylsulfonyl enones

(2) Yang, Hyeyeon a Kim, Sunggak a

a Korea Advanced Institute of Science and Technology (KAIST) (South Korea)

Author keywords

Asymmetric catalysis; Lactones; Lewis acids; Ligands; Michael additions

Indexed keywords

2 (TRIMETHYLSILYLOXY)FURAN; FURAN DERIVATIVE; LEWIS ACID; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; MUKAIYAMA MICHAEL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 40949136596 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032074 Document Type: Article

Times cited : (44)

References (55)

1
- 2742606973
- (a) Christoffers, J. Eur. J. Org. Chem. 1998, 1259.
- (1998) Eur. J. Org. Chem , pp. 1259
- Christoffers, J.¹

2
- 0035126119
- (b) Krause, N.; Hoffmann-Röder, A. Synlett 2001, 171.
- (2001) Synlett , pp. 171
- Krause, N.¹ Hoffmann-Röder, A.²

3
- 0034986283
- (c) Christoffers, J. Synlett 2001, 723.
- (2001) Synlett , pp. 723
- Christoffers, J.¹

4
- 0002573501
- (a) Narasaka, K.; Soai, K.; Mukaiyama, T. Chem. Lett. 1974, 3, 1223.
- (1974) Chem. Lett , vol.3 , pp. 1223
- Narasaka, K.¹ Soai, K.² Mukaiyama, T.³

5
- 0000776965
- (b) Narasaka, K.; Soai, K.; Aikawa, Y.; Mukaiyama, T. Bull. Soc. Chem. Jpn. 1976, 49, 779.
- (1976) Bull. Soc. Chem. Jpn , vol.49 , pp. 779
- Narasaka, K.¹ Soai, K.² Aikawa, Y.³ Mukaiyama, T.⁴

6
- 0002436782
- Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 23, 97.
- (1994) Chem. Lett , vol.23 , pp. 97
- Kobayashi, S.¹ Suda, S.² Yamada, M.³ Mukaiyama, T.⁴

7
- 0028896929
- (a) Bernardi, A.; Karamfilova, K.; Boschin, G.; Scolastico, C. Tetrahedron Lett. 1995, 36, 1363.
- (1995) Tetrahedron Lett , vol.36 , pp. 1363
- Bernardi, A.¹ Karamfilova, K.² Boschin, G.³ Scolastico, C.⁴

8
- 0030566793
- (b) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921.
- (1996) Tetrahedron Lett , vol.37 , pp. 8921
- Bernardi, A.¹ Colombo, G.² Scolastico, C.³

9
- 0033541094
- Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994.
- (1994) J. Am. Chem. Soc , vol.1999 , pp. 121
- Evans, D.A.¹ Rovis, T.² Kozlowski, M.C.³ Tedrow, J.S.⁴

10
- 0017305047
- (a) Danishefsky, S.; Kitahara, T.; Schuda, P. F.; Etheredge, S. J. J. Am. Chem. Soc. 1976, 98, 3028.
- (1976) J. Am. Chem. Soc , vol.98 , pp. 3028
- Danishefsky, S.¹ Kitahara, T.² Schuda, P.F.³ Etheredge, S.J.⁴

11
- 0000917397
- (b) Grieco, P. A.; Ohfune, Y.; Majetich, G. J. Org. Chem. 1979, 44, 3092.
- (1979) J. Org. Chem , vol.44 , pp. 3092
- Grieco, P.A.¹ Ohfune, Y.² Majetich, G.³

12
- 0030010210
- (c) Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428.
- (1996) J. Org. Chem , vol.61 , pp. 2428
- Myers, A.G.¹ McKinstry, L.²

13
- 0037139495
- (d) Movassaghi, M.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2456.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 2456
- Movassaghi, M.¹ Jacobsen, E.N.²

14
- 0002872930
- (a) Wheeler, J. W.; Happ, G. M.; Araujo, J.; Pasteeis, J. M. Tetrahedron Lett. 1972, 46, 4635.
- (1972) Tetrahedron Lett , vol.46 , pp. 4635
- Wheeler, J.W.¹ Happ, G.M.² Araujo, J.³ Pasteeis, J.M.⁴

15
- 33847799053
- (b) Rao, Y. S. Chem. Rev. 1976, 78, 625.
- (1976) Chem. Rev , vol.78 , pp. 625
- Rao, Y.S.¹

16
- 0001074831
- (c) Ravid, U.; Silverstein, R. M.; Smith, L. R. Tetrahedron 1978, 34, 1449.
- (1978) Tetrahedron , vol.34 , pp. 1449
- Ravid, U.¹ Silverstein, R.M.² Smith, L.R.³

17
- 0001001461
- (d) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603.
- (1987) J. Org. Chem , vol.52 , pp. 4603
- Bloch, R.¹ Gilbert, L.²

18
- 37049104329
- (a) Nikishin, G. I.; Svitanko, I. V.; Troyansky, E. I. J. Chem. Soc., Perkin Trans. 2 1983, 595.
- (1983) J. Chem. Soc., Perkin Trans. 2 , pp. 595
- Nikishin, G.I.¹ Svitanko, I.V.² Troyansky, E.I.³

19
- 0025143597
- (b) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509.
- (1990) Tetrahedron Lett , vol.31 , pp. 5509
- Ohkuma, T.¹ Kitamura, M.² Noyori, R.³

20
- 0000902857
- (c) Tsuboi, S. J. Org. Chem. 1998, 63, 1102.
- (1998) J. Org. Chem , vol.63 , pp. 1102
- Tsuboi, S.¹

21
- 5644267856
- (d) Monetaña, M.; García, F.; Batalla, C. Tetrahedron Lett. 2004, 45, 8549.
- (2004) Tetrahedron Lett , vol.45 , pp. 8549
- Monetaña, M.¹ García, F.² Batalla, C.³

22
- 23044508358
- (e) Teijeira, M.; Suárez, P. L.; Gómez, G.; Terán, C.; Fall, Y. Tetrahedron Lett. 2005, 46, 5889.
- (2005) Tetrahedron Lett , vol.46 , pp. 5889
- Teijeira, M.¹ Suárez, P.L.² Gómez, G.³ Terán, C.⁴ Fall, Y.⁵

23
- 0029034764
- (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607.
- (1995) Synthesis , pp. 607
- Casiraghi, G.¹ Rassu, G.²

24
- 0000379338
- (b) Szlosek, M.; Franck, X.; Figadère, B.; Cavé, A. J. Org. Chem. 1998, 63, 5169.
- (1998) J. Org. Chem , vol.63 , pp. 5169
- Szlosek, M.¹ Franck, X.² Figadère, B.³ Cavé, A.⁴

25
- 0033518561
- (c) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 669
- Evans, D.A.¹ Kozlowski, M.C.² Murry, J.A.³ Burgey, C.S.⁴ Campos, K.R.⁵ Connell, B.T.⁶ Staples, R.J.⁷

26
- 0033518571
- (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 686
- Evans, D.A.¹ Burgey, C.S.² Kozlowski, M.C.³ Tregay, S.W.⁴

27
- 0033690703
- (e) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
- (2000) Chem. Rev , vol.100 , pp. 1929
- Casiraghi, G.¹ Zanardi, F.² Appendino, G.³ Rassu, G.⁴

28
- 0025836047
- (a) Harding, E. K.; Coleman, M. T.; Liu, L. T. Tetrahedron Lett. 1991, 32, 3795.
- (1991) Tetrahedron Lett , vol.32 , pp. 3795
- Harding, E.K.¹ Coleman, M.T.² Liu, L.T.³

29
- 0027236109
- (b) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773.
- (1993) Tetrahedron Lett , vol.34 , pp. 5773
- Morimoto, Y.¹ Nishida, K.² Hayashi, Y.³ Shirahama, H.⁴

30
- 0028136764
- (c) Pelter, A.; Ward, R. S.; Sirit, A. Tetrahedron: Asymmetry 1994, 5, 1745.
- (1994) Tetrahedron: Asymmetry , vol.5 , pp. 1745
- Pelter, A.¹ Ward, R.S.² Sirit, A.³

31
- 0030567356
- (d) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 3299
- Martin, S.F.¹ Barr, K.J.²

32
- 0002691788
- (a) Kitajima, H.; Katsuki, T. Synlett 1997, 568.
- (1997) Synlett , pp. 568
- Kitajima, H.¹ Katsuki, T.²

33
- 0030781212
- (b) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015.
- (1997) Tetrahedron , vol.53 , pp. 17015
- Kitajima, H.¹ Ito, K.² Katsuki, T.³

34
- 0032499189
- (c) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165.
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1165
- Nishikori, H.¹ Ito, K.² Katsuki, T.³

35
- 0035905168
- Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203.
- (2001) Tetrahedron , vol.57 , pp. 10203
- Desimoni, G.¹ Faita, G.² Filippone, S.³ Mella, M.⁴ Zampori, M.G.⁵ Zema, M.⁶

36
- 3142753716
- Suga, H.; Kitamura, T.; Kakehi, A.; Baba, T. Chem. Commun. 2004, 1414.
- (2004) Chem. Commun , pp. 1414
- Suga, H.¹ Kitamura, T.² Kakehi, A.³ Baba, T.⁴

37
- 0037419866
- Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 1192
- Brown, S.P.¹ Goodwin, N.C.² MacMillan, D.W.C.³

38
- 34250821683
- Yang, H.; Hong, Y.-T.; Kim, S. Org. Lett. 2007, 9, 2281.
- (2007) Org. Lett , vol.9 , pp. 2281
- Yang, H.¹ Hong, Y.-T.² Kim, S.³

39
- 0002808782
- (a) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 23, 145.
- (1994) Chem. Lett , vol.23 , pp. 145
- Wada, E.¹ Yasuoka, H.² Kanemasa, S.³

40
- 0000361989
- (b) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 23, 1637.
- (1994) Chem. Lett , vol.23 , pp. 1637
- Wada, E.¹ Yasuoka, H.² Kanemasa, S.³

41
- 0002897175
- (c) Wada, E.; Pei, W.; Kanemasa, S. Chem. Lett. 1994, 23, 2345.
- (1994) Chem. Lett , vol.23 , pp. 2345
- Wada, E.¹ Pei, W.² Kanemasa, S.³

42
- 0030068385
- (d) Wada, E.; Pei, W.; Yasuoka, H.; Chin, U.; Kanemasa, S. Tetrahedron 1996, 52, 1205.
- (1996) Tetrahedron , vol.52 , pp. 1205
- Wada, E.¹ Pei, W.² Yasuoka, H.³ Chin, U.⁴ Kanemasa, S.⁵

43
- 33846170497
- (a) Zhao, J.-L.; Liu, L.; Sui, Y.; Liu, Y.-L.; Wang, D.; Chen, Y.-J. Org. Lett. 2006, 8, 6127.
- (2006) Org. Lett , vol.8 , pp. 6127
- Zhao, J.-L.¹ Liu, L.² Sui, Y.³ Liu, Y.-L.⁴ Wang, D.⁵ Chen, Y.-J.⁶

44
- 33846044748
- (b) Landa, A.; Richter, B.; Johansen, R. L.; Minkkilä, A.; Jørgensen, K. A. J. Org. Chem. 2007, 72, 240.
- (2007) J. Org. Chem , vol.72 , pp. 240
- Landa, A.¹ Richter, B.² Johansen, R.L.³ Minkkilä, A.⁴ Jørgensen, K.A.⁵

45
- 40949164373
- Typical Procedure for the Mukaiyama-Michael Reaction of 2-(Trimethylsilyloxy)furan (3) with α′- Phenylsulfonyl Enone 5a: To the flask of freshly prepared, 4R,5S)-diPhBox]Cu(OTf) 2 (5 mol, in CHCl3 (1 mL) was added a solution of α′-phenylsulfonyl enone 5a (0.11 mmol, 25 mg) in CHCl 3 (1 mL, After being stirred at r.t. for 0.5 h, the reaction mixture was cooled to 0°C, and the solution of 3 (0.22 mmol, 35 mg) in CHCl 3 (1 mL) was added to the reaction mixture. The reaction was maintained at the desired temperature until a complete consumption of the α′-phenylsulfonyl enone 5a as monitored by TLC. After completion of the reaction, the reaction was quenched with sat. aq NaHCO 3 solution, extracted with CH2Cl2, washed with H2O, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purif
- 2).

46
- 0001237617
- (a) Utaka, M.; Watabu, H.; Takeda, A. J. Org. Chem. 1987, 52, 4363.
- (1987) J. Org. Chem , vol.52 , pp. 4363
- Utaka, M.¹ Watabu, H.² Takeda, A.³

47
- 0006207191
- (b) Ronald, R. C.; Ruder, S. M.; Lillie, T. S. Tetrahedron Lett. 1987, 28, 131.
- (1987) Tetrahedron Lett , vol.28 , pp. 131
- Ronald, R.C.¹ Ruder, S.M.² Lillie, T.S.³

48
- 0027270781
- (c) Yadav, J. S.; Maniyan, P. P. Synth. Commun. 1993, 23, 2731.
- (1993) Synth. Commun , vol.23 , pp. 2731
- Yadav, J.S.¹ Maniyan, P.P.²

49
- 0030976231
- (d) Paddon-Jones, G. C.; Moore, C. J.; Brecknell, D. J.; König, W. A.; Kitching, W. Tetrahedron Lett. 1997, 38, 3479.
- (1997) Tetrahedron Lett , vol.38 , pp. 3479
- Paddon-Jones, G.C.¹ Moore, C.J.² Brecknell, D.J.³ König, W.A.⁴ Kitching, W.⁵

50
- 0037420760
- (e) Enholm, E. J.; Bhardawaj, A. Tetrahedron Lett. 2003, 44, 3763.
- (2003) Tetrahedron Lett , vol.44 , pp. 3763
- Enholm, E.J.¹ Bhardawaj, A.²

51
- 3843104976
- (f) Benincori, T.; Rizzo, S.; Pilati, T.; Ponti, A.; Sada, M.; Pagliarini, E.; Ratti, S.; Giuseppe, C.; Ferra, L.; Sannicolò, F. Tetrahedron: Asymmetry 2004, 15, 2289.
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 2289
- Benincori, T.¹ Rizzo, S.² Pilati, T.³ Ponti, A.⁴ Sada, M.⁵ Pagliarini, E.⁶ Ratti, S.⁷ Giuseppe, C.⁸ Ferra, L.⁹ Sannicolò, F.¹⁰

52
- 0001227655
- (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 5525
- Hunter, C.A.¹ Sanders, J.K.M.²

53
- 0034006954
- (b) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 1635
- Evans, D.A.¹ Johnson, J.S.² Olhava, E.J.³

54
- 30344461922
- (c) Pandey, M. K.; Bisai, A.; Singh, V. K. Tetrahedron Lett. 2006, 47, 897.
- (2006) Tetrahedron Lett , vol.47 , pp. 897
- Pandey, M.K.¹ Bisai, A.² Singh, V.K.³

55
- 33846170497
- (d) Zhao, J.-L.; Liu, L.; Sui, Y.; Liu, Y.-L.; Wang, D.; Chen, Y.-J. Org. Lett. 2006, 8, 6127.
- (2006) Org. Lett , vol.8 , pp. 6127
- Zhao, J.-L.¹ Liu, L.² Sui, Y.³ Liu, Y.-L.⁴ Wang, D.⁵ Chen, Y.-J.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.