SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 17, 2008, Pages 2647-2650

Investigation of a tandem iminium ion allylation approach to piperidines

(3) Mancey, Nicole C a Butlin, Roger J b Harrity, Joseph P A a

a UNIVERSITY OF SHEFFIELD (United Kingdom)

b ASTRAZENECA (United Kingdom)

Author keywords

Allylsilane; Annulation; Iminium ion; Lewis acid; Piperidines

Indexed keywords

ALKENE; IMINIUM ION; ION; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 55449113527 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083525 Document Type: Article

Times cited : (10)

References (35)

1
- 0002437687
- Brossi, A, Ed, Academic Press: San Diego
- (a) Strunzand, G. M.; Finlay, J. A. The Alkaloids, Vol. 26; Brossi, A., Ed.; Academic Press: San Diego, 1986, 89.
- (1986) The Alkaloids , vol.26 , pp. 89
- Strunzand, G.M.¹ Finlay, J.A.²

2
- 0842268019
- (b) Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
- (2004) Tetrahedron , vol.60 , pp. 1701
- Buffat, M.G.P.¹

3
- 0033709712
- (c) Laschat, S.; Dickner, T. Synthesis 2000, 1781.
- (2000) Synthesis , pp. 1781
- Laschat, S.¹ Dickner, T.²

4
- 18444378413
- For recent overviews, see: a
- For recent overviews, see: (a) Harrity, J. P. A.; Provoost, O. Org. Biomol. Chem. 2005, 3, 1349.
- (2005) Org. Biomol. Chem , vol.3 , pp. 1349
- Harrity, J.P.A.¹ Provoost, O.²

5
- 11844288998
- (b) Hsung, R. P.; Kurdyumov, A. V.; Sydorenko, N. Eur. J. Org. Chem. 2005, 23.
- (2005) Eur. J. Org. Chem , pp. 23
- Hsung, R.P.¹ Kurdyumov, A.V.² Sydorenko, N.³

6
- 33846500851
- (a) Movassaghi, M.; Chen, B. Angew. Chem. Int. Ed. 2007, 46, 565.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 565
- Movassaghi, M.¹ Chen, B.²

7
- 34249824279
- (b) Schmidt, A.; Gütlein, J.-P.; Mkrrchyan, S.; Görls, H.; Langer, P. Synlett 2007, 1305.
- (2007) Synlett , pp. 1305
- Schmidt, A.¹ Gütlein, J.-P.² Mkrrchyan, S.³ Görls, H.⁴ Langer, P.⁵

8
- 34247874549
- (c) Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 5334
- Chan, A.¹ Scheidt, K.A.²

9
- 33646567185
- (d) Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 6330.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 6330
- Shintani, R.¹ Hayashi, T.²

10
- 33746917485
- (e) Halliday, J. I.; Chebib, M.; Turner, P.; McLeod, M. D. Org. Lett. 2006, 8, 3399.
- (2006) Org. Lett , vol.8 , pp. 3399
- Halliday, J.I.¹ Chebib, M.² Turner, P.³ McLeod, M.D.⁴

11
- 2542457448
- (f) Agami, C.; Dechoux, L.; Hebbe, S.; Ménard, C. Tetrahedron 2004, 60, 5433.
- (2004) Tetrahedron , vol.60 , pp. 5433
- Agami, C.¹ Dechoux, L.² Hebbe, S.³ Ménard, C.⁴

12
- 4644248178
- (g) Sydorenko, N.; Hsung, R. P.; Darwish, O. S.; Hahn, J. M.; Liu, J. J. Org. Chem. 2004, 69, 6732.
- (2004) J. Org. Chem , vol.69 , pp. 6732
- Sydorenko, N.¹ Hsung, R.P.² Darwish, O.S.³ Hahn, J.M.⁴ Liu, J.⁵

13
- 0037071942
- (h) McLaughlin, M. J.; Hsung, R. P.; Cole, K. C.; Hahn, J. M.; Wang, J. Org. Lett. 2002, 4, 2017.
- (2002) Org. Lett , vol.4 , pp. 2017
- McLaughlin, M.J.¹ Hsung, R.P.² Cole, K.C.³ Hahn, J.M.⁴ Wang, J.⁵

14
- 0000546380
- (i) Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Douglas, C. J.; McLaughlin, M. J.; Mulder, J. A.; Yao, L. J. Org. Lett. 1999, 1, 509.
- (1999) Org. Lett , vol.1 , pp. 509
- Hsung, R.P.¹ Wei, L.-L.² Sklenicka, H.M.³ Douglas, C.J.⁴ McLaughlin, M.J.⁵ Mulder, J.A.⁶ Yao, L.J.⁷

15
- 0034815578
- (a) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596.
- (2001) Synlett , pp. 1596
- Hedley, S.J.¹ Moran, W.J.² Prenzel, A.H.G.P.³ Price, D.A.⁴ Harrity, J.P.A.⁵

16
- 0038441546
- (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286.
- (2003) J. Org. Chem , vol.68 , pp. 4286
- Hedley, S.J.¹ Moran, W.J.² Price, D.A.³ Harrity, J.P.A.⁴

17
- 0344824459
- (c) Moran, W. J.; Goodenough, K. M.; Raubo, P.; Harrity, J. P. A. Org. Lett. 2003, 5, 3427.
- (2003) Org. Lett , vol.5 , pp. 3427
- Moran, W.J.¹ Goodenough, K.M.² Raubo, P.³ Harrity, J.P.A.⁴

18
- 11844292757
- (d) Goodenough, K. M.; Moran, W. J.; Raubo, P.; Harrity, J. P. A. J. Org. Chem. 2005, 70, 207.
- (2005) J. Org. Chem , vol.70 , pp. 207
- Goodenough, K.M.¹ Moran, W.J.² Raubo, P.³ Harrity, J.P.A.⁴

19
- 22244488092
- (e) Goodenough, K. M.; Raubo, P.; Harrity, J. P. A. Org. Lett. 2005, 7, 2993.
- (2005) Org. Lett , vol.7 , pp. 2993
- Goodenough, K.M.¹ Raubo, P.² Harrity, J.P.A.³

20
- 33746588617
- (f) Pattenden, L. C.; Wybrow, R. A. J.; Smith, S. A.; Harrity, J. P. A. Org. Lett. 2006, 8, 3089.
- (2006) Org. Lett , vol.8 , pp. 3089
- Pattenden, L.C.¹ Wybrow, R.A.J.² Smith, S.A.³ Harrity, J.P.A.⁴

21
- 28844471334
- (g) Provoost, O. Y.; Hedley, S. J.; Hazelwood, A. J.; Harrity, J. P. A. Tetrahedron Lett. 2006, 47, 331.
- (2006) Tetrahedron Lett , vol.47 , pp. 331
- Provoost, O.Y.¹ Hedley, S.J.² Hazelwood, A.J.³ Harrity, J.P.A.⁴

22
- 33746588617
- (h) Pattenden, L. C.; Wybrow, R. A. J.; Smith, S. A.; Harrity, J. P. A. Org. Lett. 2006, 8, 3089.
- (2006) Org. Lett , vol.8 , pp. 3089
- Pattenden, L.C.¹ Wybrow, R.A.J.² Smith, S.A.³ Harrity, J.P.A.⁴

23
- 39149104005
- (i) Pattenden, L. C.; Adams, H.; Smith, S. A.; Harrity, J. P. A. Tetrahedron 2008, 64, 2951.
- (2008) Tetrahedron , vol.64 , pp. 2951
- Pattenden, L.C.¹ Adams, H.² Smith, S.A.³ Harrity, J.P.A.⁴

24
- 33845953429
- For a similar strategy to pyrans, see
- For a similar strategy to pyrans, see: Epstein, O. L.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 16480.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 16480
- Epstein, O.L.¹ Rovis, T.²

25
- 0025771936
- (a) Guyot, B.; Pornet, J.; Miginiac, L. Tetrahedron 1991, 47, 3981.
- (1991) Tetrahedron , vol.47 , pp. 3981
- Guyot, B.¹ Pornet, J.² Miginiac, L.³

26
- 0346333517
- (b) Princet, B.; Anselme, G.; Pornet, J. J. Organomet. Chem. 1999, 592, 34.
- (1999) J. Organomet. Chem , vol.592 , pp. 34
- Princet, B.¹ Anselme, G.² Pornet, J.³

27
- 33645494788
- A related approach that employs the addition of α-methylstyrene to an ammonium chloride/formaldehyde mixture has been used to prepare the piperidine core of haloperidol: Janssen, P. A. J, van de Westeringh, C, Jageneau, A. H. M, Demoen, P. J. A, Hermans, B. K. F, van Daele, G. H. P, Schellekens, K. H. L, van der Eycken, C. A. M, Niemegeers, C. J. E. J. Med. Pharm. Chem. 1959, 1, 281
- A related approach that employs the addition of α-methylstyrene to an ammonium chloride/formaldehyde mixture has been used to prepare the piperidine core of haloperidol: Janssen, P. A. J.; van de Westeringh, C.; Jageneau, A. H. M.; Demoen, P. J. A.; Hermans, B. K. F.; van Daele, G. H. P.; Schellekens, K. H. L.; van der Eycken, C. A. M.; Niemegeers, C. J. E. J. Med. Pharm. Chem. 1959, 1, 281.

28
- 0033617174
- Katritzky, A. R.; Luo, Z.; Cui, X.-L. J. Org. Chem. 1999, 64, 3328.
- (1999) J. Org. Chem , vol.64 , pp. 3328
- Katritzky, A.R.¹ Luo, Z.² Cui, X.-L.³

29
- 33845377356
- Shono, T.; Matsumura, Y.; Uchida, K.; Kobayashi, H. J. Org. Chem. 1985, 50, 3243.
- (1985) J. Org. Chem , vol.50 , pp. 3243
- Shono, T.¹ Matsumura, Y.² Uchida, K.³ Kobayashi, H.⁴

30
- 20444481574
- Brimble, M. A.; Brocke, C. Eur. J. Org. Chem. 2005, 2385.
- (2005) Eur. J. Org. Chem , pp. 2385
- Brimble, M.A.¹ Brocke, C.²

31
- 0042251512
- Aizpurua, J. M.; Palomo, C.; Palomo, A. L. Can. J. Chem. 1984, 62, 336.
- (1984) Can. J. Chem , vol.62 , pp. 336
- Aizpurua, J.M.¹ Palomo, C.² Palomo, A.L.³

32
- 55449095978
- The low yields of product appear to be due to competing addition of BSA to 5. Indeed, addition of BSA (1 equiv) to a mixture of 5 and TMSOTf (1 equiv) in the absence of allylsilane 1 resulted in <20% recovery of 5 together with unidentified material.
- The low yields of product appear to be due to competing addition of BSA to 5. Indeed, addition of BSA (1 equiv) to a mixture of 5 and TMSOTf (1 equiv) in the absence of allylsilane 1 resulted in <20% recovery of 5 together with unidentified material.

33
- 0041540779
- For an excellent discussion and lead references, see
- For an excellent discussion and lead references, see: Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254.
- (1997) J. Org. Chem , vol.62 , pp. 5254
- Organ, M.G.¹ Winkle, D.D.² Huffmann, J.³

34
- 55449112596
- Representative Experimental Procedure for the Preparation of [3+3]-Cycloaddition Adducts; Synthesis of 7-Methylenehexahydroindolizin-3(5H)-one (7, To a solution of 5 (60 mg, 0.35 mmol, 1 equiv) in CH2Cl2 (1.5 mL) at -78 °C was added 1 (69 mg, 0.35 mmol, 1 equiv) in CH2Cl2 (1.5 mL) followed by TMSOTf (0.03 mL, 0.17 mmol, 0.5 equiv, The reaction was left at -78 °C for 1 h before being warmed to r.t. After 16 h, the reaction was quenched with aq NaHCO3 solution and extracted with CH2Cl2. The organic layers were washed with brine before drying over MgSO4. The reaction was concentrated in vacuo. Purification by silica gel chromatography provided 7 as a mixture of isomers (44 mg, 84, exo/endo, 1:4, FTIR: 3055 (m, 2986 (m, 2685 (w, 1686 (s, 1668 (s, 1422 (m, 1266 (s) cm-1. 1H NMR 250 MHz, CDCl3, δ, 1.50
- 13NO: 151.0997; found: 151.0999.

35
- 0013570749
- For comparative spectroscopic data of exo-7, see: Gelas-Mialhe, Y.; Gramain, J. C.; Hajouji, H.; Remuson, R. Heterocycles 1992, 34, 37.
- (b) For comparative spectroscopic data of exo-7, see: Gelas-Mialhe, Y.; Gramain, J. C.; Hajouji, H.; Remuson, R. Heterocycles 1992, 34, 37.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.