SCOPUS 정보 검색 플랫폼

Volumn , Issue 8, 2008, Pages 1175-1178

Dess-Martin periodinane promoted oxidative coupling of Baylis-Hillman adducts with silyl enol ethers: A novel synthesis of cis-fused dihydropyrans

(6) Yadav, J S a Subba Reddy, B V a Mandal, S S a Basak, A K a Madavi, C a Kunwar, A C a

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

Author keywords

Baylis Hillman adducts; Enol ethers; Hypervalent iodine; Oxidative Mukaiyama Michael addition

Indexed keywords

PYRAN DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLIZATION; DESS MARTIN OXIDATION; DIELS ALDER REACTION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 44349130265 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072730 Document Type: Article

Times cited : (10)

References (35)

1
- 0034141601
- (a) Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 7.
- (2000) Nat. Prod. Rep , vol.17 , pp. 7
- Faulkner, D.J.¹

2
- 0034966749
- (b) Roush, W. R.; Dilley, G. J. Synlett 2001, 955.
- (2001) Synlett , pp. 955
- Roush, W.R.¹ Dilley, G.J.²

3
- 0001399971
- (c) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041.
- (1995) Chem. Rev , vol.95 , pp. 2041
- Norcross, R.D.¹ Paterson, I.²

4
- 0035807553
- (d) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 3149.
- (2001) Org. Lett , vol.3 , pp. 3149
- Paterson, I.¹ De Savi, C.² Tudge, M.³

5
- 0001546043
- (a) Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 112, 3702.
- (2000) Angew. Chem. Int. Ed , vol.112 , pp. 3702
- Jørgensen, K.A.¹

6
- 0033936085
- (b) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
- (2000) Acc. Chem. Res , vol.33 , pp. 325
- Johnson, J.S.¹ Evans, D.A.²

7
- 0032772355
- (c) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605.
- (1999) Acc. Chem. Res , vol.32 , pp. 605
- Jørgensen, K.A.¹ Johannsen, M.² Yao, S.³ Audrain, H.⁴ Thorhauge, J.⁵

8
- 44349113852
- (d) Gademann, D. E.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2002, 112, 3702.
- (2002) Angew. Chem. Int. Ed , vol.112 , pp. 3702
- Gademann, D.E.¹ Chavez, D.E.² Jacobsen, E.N.³

9
- 44349188330
- DE 2155113, 34174q
- Baylis, A. B.; Hillman, M. E. D. DE 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
- (1972) Chem. Abstr , vol.77
- Baylis, A.B.¹ Hillman, M.E.D.²

10
- 0037366617
- (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
- (2003) Chem. Rev , vol.103 , pp. 811
- Basavaiah, D.¹ Rao, A.J.² Satyanarayana, T.³

11
- 0342419508
- (b) Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001.
- (1996) Tetrahedron , vol.52 , pp. 8001
- Basavaiah, D.¹ Dharma Rao, P.² Suguna Hyma, R.³

12
- 4744362831
- (c) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
- (1988) Tetrahedron , vol.44 , pp. 4653
- Drewes, S.E.¹ Roos, G.H.P.²

13
- 0042530225
- (a) Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2003, 44, 6737.
- (2003) Tetrahedron Lett , vol.44 , pp. 6737
- Lee, K.Y.¹ Kim, J.M.² Kim, J.N.³

14
- 0037434036
- (b) Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron 2003, 59, 385.
- (2003) Tetrahedron , vol.59 , pp. 385
- Lee, K.Y.¹ Kim, J.M.² Kim, J.N.³

15
- 0037189133
- (c) Im, Y. J.; Lee, K. Y.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2002, 43, 4675.
- (2002) Tetrahedron Lett , vol.43 , pp. 4675
- Im, Y.J.¹ Lee, K.Y.² Kim, T.H.³ Kim, J.N.⁴

16
- 0038294333
- (d) Kim, J. N.; Kim, J. M.; Lee, K. Y. Synlett 2003, 821.
- (2003) Synlett , pp. 821
- Kim, J.N.¹ Kim, J.M.² Lee, K.Y.³

17
- 0035914494
- (e) Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341.
- (2001) Tetrahedron Lett , vol.42 , pp. 8341
- Kim, J.N.¹ Kim, H.S.² Gong, J.H.³ Chung, Y.M.⁴

18
- 37049094623
- (a) Drewes, S. E.; Emslie, N. D. J. Chem. Soc., Perkin Trans. 1 1982, 2079.
- (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 2079
- Drewes, S.E.¹ Emslie, N.D.²

19
- 84986397396
- (b) Hoffmann, H. M. R.; Rabe, J. Helv. Chim. Acta 1984, 67, 413.
- (1984) Helv. Chim. Acta , vol.67 , pp. 413
- Hoffmann, H.M.R.¹ Rabe, J.²

20
- 18244387510
- (c) Hoffmann, H. M. R.; Rabe, J. J. Org. Chem. 1985, 50, 3849.
- (1985) J. Org. Chem , vol.50 , pp. 3849
- Hoffmann, H.M.R.¹ Rabe, J.²

21
- 0021921867
- (a) Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
- (1985) Angew. Chem., Int. Ed. Engl , vol.24 , pp. 94
- Hoffmann, H.M.R.¹ Rabe, J.²

22
- 0025863805
- (b) Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213.
- (1991) Helv. Chim. Acta , vol.74 , pp. 1213
- Buchholz, R.¹ Hoffmann, H.M.R.²

23
- 37049095518
- (c) Ameer, F.; Drewes, S. E.; Hoole, R. F. A.; Kaye, P. T.; Pitchford, A. T. J. Chem. Soc., Perkin Trans. 1 1985, 2713.
- (1985) J. Chem. Soc., Perkin Trans. 1 , pp. 2713
- Ameer, F.¹ Drewes, S.E.² Hoole, R.F.A.³ Kaye, P.T.⁴ Pitchford, A.T.⁵

24
- 0003579937
- Academic Press: San Diego
- (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997, 256.
- (1997) Hypervalent Iodine in Organic Synthesis , pp. 256
- Varvoglis, A.¹

25
- 0032821239
- (b) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271.
- (1999) Synthesis , pp. 1271
- Wirth, T.¹ Hirt, U.H.²

26
- 0035800351
- (c) Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812.
- (2001) Angew. Chem. Int. Ed , vol.40 , pp. 2812
- Wirth, T.¹

27
- 33644528891
- (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
- (1983) J. Org. Chem , vol.48 , pp. 4155
- Dess, D.B.¹ Martin, J.C.²

28
- 3042741556
- (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 7277
- Dess, D.B.¹ Martin, J.C.²

29
- 0037070617
- (a) Nicolaou, K. C.; Baran, P. S.; Zong, Y.-L.; Sugita, K. J. Am. Chem. Soc. 2002, 124, 2212.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 2212
- Nicolaou, K.C.¹ Baran, P.S.² Zong, Y.-L.³ Sugita, K.⁴

30
- 25144513578
- (b) Nicolaou, K. C.; Mathison, C. J. N. Angew. Chem. Int. Ed. 2005, 44, 5992.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 5992
- Nicolaou, K.C.¹ Mathison, C.J.N.²

31
- 0342615043
- (c) Chaudhari, S. S. Synlett 2000, 278.
- (2000) Synlett , pp. 278
- Chaudhari, S.S.¹

32
- 31844432220
- (d) Ladziata, U.; Zhdankin, V. V. ARKIVOC 2006, (ix), 26.
- (2006) ARKIVOC , vol.9 , pp. 26
- Ladziata, U.¹ Zhdankin, V.V.²

33
- 0035806283
- (e) Lawrence, J. N.; Crump, J. P.; McGown, A. T.; Hadfield, J. A. Tetrahedron Lett. 2001, 42, 3939.
- (2001) Tetrahedron Lett , vol.42 , pp. 3939
- Lawrence, J.N.¹ Crump, J.P.² McGown, A.T.³ Hadfield, J.A.⁴

34
- 44349145778
- General Experimental Procedure A mixture of Baylis-Hillman adduct (1 mmol, DMP (1.2 mmol, and pyridine (1.5 mmol) in anhyd CH2Cl 2 (10 mL) was stirred at r.t. until complete oxidation took place. To this, trimethylsilyl enol ether (1.5 mmol) was added and stirred until complete addition (as indicated by TLC) took place. The reaction mixture was diluted with H2O (50 mL) and extracted with Et2O (3 x 15 mL, The combined ether layer was washed with sat. aq NaHCO3 soln (1 x 15 mL, brine (1 x 10 mL, dried over Na2SO4, and evaporated. The crude product was purified by silica gel column chromatography using a gradient mixture of hexane-EtOAc (9:1) as eluent to afford pure substituted dihydropyran derivatives. Spectral Data of Selected Compounds Compound 3a (Table 1, colorless liquid. IR KBr, νmax, 2954, 2838, 1738, 1454, 1234, 1207, 1153, 1017, 781 cm-1. 1H NM
- 4NaCl: 367.0713; found: 367.0715.

35
- 0029887561
- Horiguchi, Y.; Sano, T.; Tsuda, Y. Chem. Pharm. Bull. 1996, 44, 670.
- (1996) Chem. Pharm. Bull , vol.44 , pp. 670
- Horiguchi, Y.¹ Sano, T.² Tsuda, Y.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.