SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 1, 2009, Pages 89-91

Mild stereoselective hydrohalogenation leading to (Z)-halopropenamides at room temperature

(3) Feray, Laurence a Perfetti, Patricia a Bertrand, Michèle P a

a AIX MARSEILLE UNIVERSITY (France)

Author keywords

(Z) halopropenamides; (Z) halopropenoic esters; Hydrohalogenation; Tert butyl halide; Zinc halide

Indexed keywords

EID: 62349093375 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087489 Document Type: Article

Times cited : (12)

References (36)

1
- 0035955025
- For Sonogashira coupling reaction, see: a
- For Sonogashira coupling reaction, see: (a) Eichberg, M. J.; Dorta, R. L.; Grotjahn, D. B.; Lamottke, K.; Schmidt, M.; Vollhardt, K. P. C. J. Am. Chem. Soc. 2001, 123, 9324.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 9324
- Eichberg, M.J.¹ Dorta, R.L.² Grotjahn, D.B.³ Lamottke, K.⁴ Schmidt, M.⁵ Vollhardt, K.P.C.⁶

2
- 0037131956
- (b) Fiandanese, V.; Babudri, F.; Marchese, G.; Punzi, A. Tetrahedron 2002, 58, 9547.
- (2002) Tetrahedron , vol.58 , pp. 9547
- Fiandanese, V.¹ Babudri, F.² Marchese, G.³ Punzi, A.⁴

3
- 1242318515
- (c) Cherry, K.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2004, 45, 2063.
- (2004) Tetrahedron Lett , vol.45 , pp. 2063
- Cherry, K.¹ Thibonnet, J.² Duchêne, A.³ Parrain, J.-L.⁴ Abarbri, M.⁵

4
- 13444293345
- (d) Cramer, N.; Laschat, S.; Baro, A.; Schwalbe, H.; Richter, C. Angew. Chem. Int. Ed. 2005, 44, 820.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 820
- Cramer, N.¹ Laschat, S.² Baro, A.³ Schwalbe, H.⁴ Richter, C.⁵

5
- 33644930823
- (e) Cramer, N.; Buchweitz, M.; Laschat, S.; Frey, W.; Baro, A.; Mathieu, D.; Richter, C.; Schwalbe, H. Chem. Eur. J. 2006, 12, 2488.
- (2006) Chem. Eur. J , vol.12 , pp. 2488
- Cramer, N.¹ Buchweitz, M.² Laschat, S.³ Frey, W.⁴ Baro, A.⁵ Mathieu, D.⁶ Richter, C.⁷ Schwalbe, H.⁸

6
- 0032514457
- For Stille coupling reaction, see: f
- For Stille coupling reaction, see: (f) Mcdonald, G.; Alcaraz, L.; Wei, X.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron 1998, 54, 9823.
- (1998) Tetrahedron , vol.54 , pp. 9823
- Mcdonald, G.¹ Alcaraz, L.² Wei, X.³ Lewis, N.J.⁴ Taylor, R.J.K.⁵

7
- 0038646645
- (g) Cherry, K.; Abarbri, M.; Parrain, J.-L.; Duchêne, A. Tetrahedron Lett. 2003, 44, 5791.
- (2003) Tetrahedron Lett , vol.44 , pp. 5791
- Cherry, K.¹ Abarbri, M.² Parrain, J.-L.³ Duchêne, A.⁴

8
- 24944538375
- (h) Cherry, K.; Duchêne, A.; Thibonnet, J.; Parrain, J.-L.; Abarbri, M. Synthesis 2005, 2349.
- (2005) Synthesis , pp. 2349
- Cherry, K.¹ Duchêne, A.² Thibonnet, J.³ Parrain, J.-L.⁴ Abarbri, M.⁵

9
- 0001044764
- For coupling reaction with organozirconocenes, see: i
- For coupling reaction with organozirconocenes, see: (i) Crombie, L.; Hobbs, A. J. W.; Horsham, M. A. Tetrahedron Lett. 1987, 28, 4875.
- (1987) Tetrahedron Lett , vol.28 , pp. 4875
- Crombie, L.¹ Hobbs, A.J.W.² Horsham, M.A.³

10
- 0025908348
- (j) Rossi, R.; Carpita, A.; Lippolis, V. Synth. Commun. 1991, 21, 333.
- (1991) Synth. Commun , vol.21 , pp. 333
- Rossi, R.¹ Carpita, A.² Lippolis, V.³

11
- 0000086173
- For annulation of allenes, see: k
- For annulation of allenes, see: (k) Larock, R. C.; He, Y.; Leong, W. W.; Han, X.; Refvik, M. D.; Zenner, J. M. J. Org. Chem. 1998, 63, 2154.
- (1998) J. Org. Chem , vol.63 , pp. 2154
- Larock, R.C.¹ He, Y.² Leong, W.W.³ Han, X.⁴ Refvik, M.D.⁵ Zenner, J.M.⁶

12
- 0000797408
- (a) Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S. Tetrahedron 1989, 45, 3557.
- (1989) Tetrahedron , vol.45 , pp. 3557
- Grigg, R.¹ Sridharan, V.² Stevenson, P.³ Sukirthalingam, S.⁴

13
- 0035903946
- (b) Kiewel, K.; Tallant, M.; Sulikowski, G. A. Tetrahedron Lett. 2001, 42, 6621.
- (2001) Tetrahedron Lett , vol.42 , pp. 6621
- Kiewel, K.¹ Tallant, M.² Sulikowski, G.A.³

14
- 0042626234
- (c) Mori, M.; Nakanishi, M.; Kajishima, D.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 9801.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 9801
- Mori, M.¹ Nakanishi, M.² Kajishima, D.³ Sato, Y.⁴

15
- 39149118885
- Ikoma, M.; Oikawa, M.; Sasaki, M. Tetrahedron 2008, 64, 2740.
- (2008) Tetrahedron , vol.64 , pp. 2740
- Ikoma, M.¹ Oikawa, M.² Sasaki, M.³

16
- 0742321841
- Han, C.; Shen, R.; Su, S.; Porco, J. A. Jr. Org. Lett. 2004, 6, 27.
- (2004) Org. Lett , vol.6 , pp. 27
- Han, C.¹ Shen, R.² Su, S.³ Porco Jr., J.A.⁴

17
- 0001183140
- (a) Bey, P.; Vevert, J. P. J. Org. Chem. 1980, 45, 3249.
- (1980) J. Org. Chem , vol.45 , pp. 3249
- Bey, P.¹ Vevert, J.P.²

18
- 33846922856
- (b) Ge, C. S.; Hourcade, S.; Ferdenzi, A.; Chiaroni, A.; Mons, S.; Delpech, B.; Marazano, C. Eur. J. Org. Chem. 2006, 4106.
- (2006) Eur. J. Org. Chem , pp. 4106
- Ge, C.S.¹ Hourcade, S.² Ferdenzi, A.³ Chiaroni, A.⁴ Mons, S.⁵ Delpech, B.⁶ Marazano, C.⁷

19
- 84981795044
- For the preparation of (E)-3-bromopropenamides via the reaction of 3-aminopropynal with HBr followed by rearrangement, see: (a) Neuenschwander, M.; Hafner, K. Angew. Chem., Int. Ed. Engl. 1968, 7, 460.
- For the preparation of (E)-3-bromopropenamides via the reaction of 3-aminopropynal with HBr followed by rearrangement, see: (a) Neuenschwander, M.; Hafner, K. Angew. Chem., Int. Ed. Engl. 1968, 7, 460.

20
- 0000137232
- (b) Gais, H.-J.; Hafner, K.; Neuenschwander, M. Helv. Chim. Acta 1969, 52, 2641.
- (1969) Helv. Chim. Acta , vol.52 , pp. 2641
- Gais, H.-J.¹ Hafner, K.² Neuenschwander, M.³

21
- 0013440033
- (c) Niederhauser, A.; Neuenschwander, M. Helv. Chim. Acta 1973, 56, 1318.
- (1973) Helv. Chim. Acta , vol.56 , pp. 1318
- Niederhauser, A.¹ Neuenschwander, M.²

22
- 0346099779
- For the synthesis of (E)- or (Z)-iodopropenamides via peptide coupling reaction between the corresponding (E)- or (Z)-iodopropenoic acids and an amine, see refs. 1d, 3, 4. For aminolysis of acyl chlorides prepared from 3-bromo- or 3-iodopropenoic acids leading to a mixture of Z- and E-isomers, see: (d) Wilson, R. M.; Commons, T. J. J. Org. Chem. 1975, 40, 2891.
- For the synthesis of (E)- or (Z)-iodopropenamides via peptide coupling reaction between the corresponding (E)- or (Z)-iodopropenoic acids and an amine, see refs. 1d, 3, 4. For aminolysis of acyl chlorides prepared from 3-bromo- or 3-iodopropenoic acids leading to a mixture of Z- and E-isomers, see: (d) Wilson, R. M.; Commons, T. J. J. Org. Chem. 1975, 40, 2891.

23
- 0345860839
- (e) Wojcik, J.; Witanowski, M. J. Mol. Struct. 1978, 49, 249.
- (1978) J. Mol. Struct , vol.49 , pp. 249
- Wojcik, J.¹ Witanowski, M.²

24
- 0007704990
- Fujisawa, T.; Tanaka, A.; Ukaji, Y. Chem. Lett. 1989, 1255.
- (1989) Chem. Lett , pp. 1255
- Fujisawa, T.¹ Tanaka, A.² Ukaji, Y.³

25
- 0025690414
- (a) Ma, S.; Lu, X. Tetrahedron Lett. 1990, 31, 7653.
- (1990) Tetrahedron Lett , vol.31 , pp. 7653
- Ma, S.¹ Lu, X.²

26
- 33751392551
- (b) Ma, S.; Lu, X.; Li, Z. J. Org. Chem. 1992, 57, 709.
- (1992) J. Org. Chem , vol.57 , pp. 709
- Ma, S.¹ Lu, X.² Li, Z.³

27
- 62349121873
- For the use of NaI in AcOH, see
- (c) For the use of NaI in AcOH, see: Marek, I.; Alexakis, A.; Normant, J.-F. Tetrahedron Lett. 1992, 33, 5329.
- (1992) Tetrahedron Lett , vol.33 , pp. 5329
- Marek, I.¹ Alexakis, A.² Normant, J.-F.³

28
- 62349104821
- The reactions were generally performed at 90°C over 22-48 h. At 70°C lower yields were obtained (see ref. 8b).
- The reactions were generally performed at 90°C over 22-48 h. At 70°C lower yields were obtained (see ref. 8b).

29
- 48749107507
- Feray, L.; Bertrand, M. P. Eur. J. Org. Chem. 2008, 3164.
- (2008) Eur. J. Org. Chem , pp. 3164
- Feray, L.¹ Bertrand, M.P.²

30
- 62349141707
- Using only 2 equivalents of tert-butyl iodide led to lower yields
- Using only 2 equivalents of tert-butyl iodide led to lower yields.

31
- 0026743316
- De la Pradilla, R. F.; Morente, M.; Paley, R. S. Tetrahedron Lett. 1992, 33, 6101.
- (1992) Tetrahedron Lett , vol.33 , pp. 6101
- De la Pradilla, R.F.¹ Morente, M.² Paley, R.S.³

32
- 62349108441
- This might be correlated to the relative basicity of amides and sulfoxides
- This might be correlated to the relative basicity of amides and sulfoxides.

33
- 62349117851
- Z)-N,N-Diallyl-3-iodoacrylamide(2d, Typical Procedure To a solution of N,N-diallyl-3-propynamide (50 mg, 0.335 mmol) in CH2Cl2 (1.7 mL) were added t-BuI (200 μL, 1.67 mmol, 3 equiv) and ZnI2 (214 mg, 0.67 mmol, 2 equiv) at r.t. After 18 h, H2O (5 mL) was added, and the reaction mixture was extracted twice with CH2Cl2. The organic layers were dried over MgSO4, filtered, and concentrated under reduce pressure. Flash chromatography on SiO2 (100% pentane then 100% Et2O) afforded 2d (81 mg, 0.293 mmol, 87, 1H NMR (300 MHz, δ, 3.85 (br d, J, 5.1 Hz, 2 H, 4.05 (br d, J, 5.9 Hz, 2 H, 5.11-5.28 (m, 4 H, 5.68-5.89 (m, 2 H, 6.85 (d, J, 8.8 Hz, 1 H, 7.10 (d, J, 8.8 Hz, 1 H, 13C NMR (75 MHz, δ, 47.4 (CH2, 49.9 CH2, 87.6, CHI, 117.9
- +: 278.0036; found: 278.0035.

34
- 0000996577
- Taniguchi, M.; Kobayashi, S.; Nakagawa, M.; Hino, T. Tetrahedron Lett. 1986, 27, 4763.
- (1986) Tetrahedron Lett , vol.27 , pp. 4763
- Taniguchi, M.¹ Kobayashi, S.² Nakagawa, M.³ Hino, T.⁴

35
- 62349128716
- Owing to complexation of the product to zinc salts, the olefinic protons are more deshielded in the crude reaction mixture - before aqueous treatment - than in the pure isolated product 2d (δ = 7.0 ppm and 7.4 ppm with a coupling constant equal to 9.1 Hz: 6.85 ppm and 7.10 ppm with a coupling constant equal to 8.8 Hz, respectively).
- Owing to complexation of the product to zinc salts, the olefinic protons are more deshielded in the crude reaction mixture - before aqueous treatment - than in the pure isolated product 2d (δ = 7.0 ppm and 7.4 ppm with a coupling constant equal to 9.1 Hz: 6.85 ppm and 7.10 ppm with a coupling constant equal to 8.8 Hz, respectively).

36
- 62349130249
- Using zinc bromide led to degradation of benzylic and propargylic esters
- Using zinc bromide led to degradation of benzylic and propargylic esters.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.