References and Notes
1a
Perlmuter P. In
Conjugate Addition Reaction in Organic Synthesis, In Tetrahedron Organic Chemistry Series, No. 9
Pergamon Press;
Oxford:
1992.
p.1
1b
Helmchen G.
Hoffmann RW.
Mulzer J.
Schaumann E. In
Stereoselective Synthesis. Houben-Weyl, Methods of Organic Chemistry
Vol. E21b, 4th ed.:
Georg Thieme Verlag;
Stuttgart:
1995.
p.1041
2a
Knochel P.
Singer RD.
Chem. Rev.
1993,
93:
2117
2b
Knochel P.
Prea JA.
Jones P.
Tetrahedron
1998,
54:
8275
3a
Duursma A.
Minnaard AJ.
Feringa BL.
J. Chem. Soc.
2003,
125:
3700
3b
Hird AW.
Hoveyda AH.
Angew. Chem. Int. Ed.
2003,
42:
1276
3c
Degrado SJ.
Mizutani H.
Hoveyda AH.
J. Am. Chem. Soc.
2002,
124:
13362
3d
Gallo E.
Ragaini F.
Licia B.
Piarulli U.
J. Organomet. Chem.
2004,
689:
2169
3e
Knopff O.
Alexakis A.
Org. Lett.
2002,
4:
3835
3f
Mampreian DM.
Hoveyda AD.
Org. Lett.
2004,
6:
2829
3g
Bräse S.
Höfener S.
Angew. Chem. Int. Ed.
2005,
44:
7879
3h
Sibi MP.
Manyem S.
Tetrahedron
2000,
56:
8033
4a
Lipshutz BH.
Wood MR.
Tirado R.
J. Am. Chem. Soc.
1995,
11:
6126
4b
Maezaki N.
Sawamto H.
Yoshigami R.
Suzuki T.
Tanaka T.
Org. Lett.
2003,
5:
1345
4c
Yuguchi M.
Tokuda M.
Orito K.
Chem. Lett.
2004,
33:
674
4d
Yuguchi M.
Tokuda M.
Orito K.
Bull. Chem. Soc. Jpn.
2004,
1031
5a
Ongeri S.
Piarulli U.
Jackson RFW.
Gennari C.
Eur. J. Org. Chem.
2001,
803
5b
Berner OM.
Tedeschi L.
Enders D.
Eur. J. Org. Chem.
2002,
1877
6a
Namboothiri INN.
Hassner A.
J. Organomet. Chem.
1996,
518:
69
6b
Yao C.-F.
Kao K.-H.
Liu J.-T.
Chu C.-M.
Wang Y.
Tetrahedron
1998,
54:
791
7
Ashwood MS.
Bell LA.
Houghton PG.
Wright SHB.
Synthesis
1988,
379
8
Knochel P.
Seebach D.
Tetrahedron Lett.
1981,
22:
3223
9
Pecunioso A.
Menicagli R.
J. Org. Chem.
1988,
53:
45
10
Zhang JM.
Zhang YM.
Chin. J. Chem.
2002,
20:
296
11
Bao WL.
Zheng YF.
Zhang YM.
J. Chem. Res., Synop.
1999,
732
12
Kumar HMS.
Reddy BVS.
Reddy PT.
Yadav JS.
Tetrahedron Lett.
1999,
40:
5387
13a
Wang J.-X.
Fu Y.
Hu YL.
Angew. Chem. Int. Ed.
2002,
41:
2757
13b
Wang J.-X.
Wang K.
Zhao L.
Fu Y.
Hu YL.
Adv. Synth. Catal.
2006,
348:
1262
13c
Hu YL.
Yu JH.
Yang S.
Wang J.-X.
Synlett
1998,
1213
14a
Hu YL.
Yu JH.
Wang J.-X.
Yin YQ.
Synth. Commun.
1998,
28:
2793
14b
Hu YL.
Yu JH.
Wang J.-X.
Yin YQ.
Chin. Chem. Lett.
1998,
9:
699
14c
Huang DF.
Yang Y.
Wang J.-X.
Hu YL.
J. Chem. Res., Synop.
2002,
79
15
Wang J.-X.
Jia XF.
Meng TJ.
Xin L.
Synthesis
2005,
2838
16
Menicagli R.
Samaritani S.
Tetrahedron
1996,
52:
1425
17
Berk SC.
Jeong MCPN.
Knochel P.
Organometallics
1990,
9:
3053
18 General Procedure for the Reaction: Organozinc halides RZnX (8 mmol and 10 mmol for allyl bromide and benzyl bromide, respectively) were prepared according to Knochel’s procedure.
[17]
The solvent (THF) was removed in vacuo and then the nitroalkene (4 mmol) was added slowly. The resulting reaction mixture was stirred for the duration of the given time. After complete conversion, as indicated by TLC, sat. NH4Cl solution (10 mL) and Et2O (10 mL) were added and the mixture was stirred for 10 min. The organic layer was separated and washed with sat. brine (10 mL), dried over anhyd MgSO4 and concentrated. The pure product was obtained by column chromatography of the crude mixture on silica gel using PE-EtOAc as eluent.
19 1-Nitro-2-phenylpent-4-ene (2a): pale yellow oil. IR (KBr): 3073, 3030, 2922, 2853, 1641, 1548, 1451, 1434 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.17-7.34 (m, 5 H), 5.60-5.70 (m, 1 H), 5.02-5.09 (m, 2 H), 4.51-4.64 (m, 2 H), 3.52-3.60 (m, 1 H), 2.38-2.56 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 134.1, 128.8, 127.6, 127.4, 118.1, 79.8, 43.7, 37.6. EI-MS: m/z = 241 [M+], 211, 104, 91, 77. Anal. Calcd for C11H13NO2: C, 69.09; H, 6.85; N, 7.32. Found: C, 68.46; H, 6.93; N, 6.57.
20 1-Nitro-3-phenyl-2-(2-furyl)propane (3l): yellow oil. IR (KBr): 3063, 3030, 2924, 2860, 1551, 1501, 1451, 1431cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.37 (dd, J = 0.8, 2.0 Hz, 1 H), 7.20-7.30 (m, 3 H), 7.06-7.08 (m, 2 H), 6.26-6.27 (m, 1 H), 6.03-6.04 (m, 1 H), 4.61 (dd, J = 8.0, 12.8 Hz, 1 H), 4.52 (dd, J = 6.4, 12.8 Hz, 1 H), 3.85-3.92 (m, 1 H), 3.11 (dd, J = 7.6, 13.6 Hz, 1 H), 2.94 (dd, J = 7.6, 13.6 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 151.9, 142.2, 137.4, 129.0, 128.6, 127.0, 110.4, 107.5, 77.3, 39.6, 37.3. EI-MS: m/z = 231 [M+], 184, 91, 77. Anal. Calcd for C13H13NO3: C, 67.52; H, 5.67; N, 6.06. Found: C, 68.16; H, 5.27; N, 5.40.