References and Notes
1a
Dellaria JF.
Maki RG.
Stein HH.
Cohen J.
Whittern D.
Marsh K.
Hoffman DJ.
Plattner JJ.
Perun TJ.
J. Med. Chem.
1990,
33:
534
1b
Tao M.
Bihovsky R.
Wells GJ.
Mallamo JP.
J. Med. Chem.
1998,
41:
3912
2
Stowasser B.
Budt K.-H.
Li J.-Q.
Peyman A.
Ruppert D.
Tetrahedron
Lett.
1992,
33:
6625
3
Snoeck R.
Holy A.
Dewolf-Peeters C.
Van Den Oord J.
De Clercq E.
Andrei G.
Antimicrob. Agents Chemother.
2002,
46:
3356
4a
Peters ML.
Leonard M.
Licata AA.
Cleve Clin. J. Med.
2001,
68:
945
4b
Leder BZ.
Kronenberg HM.
Gastroenterology
2000,
119:
866
5a
Rawlings JB.
Nat. Prod. Rep.
1999,
16:
425
5b
Staunton J.
Weissman KJ.
Nat. Prod. Rep.
2001,
18:
380
5c
Paterson I.
Scott JP.
J. Chem. Soc., Perkin
Trans. 1
1999,
1003
5d
Keck D.
Bräse S.
Org. Biomol. Chem.
2006,
4:
3574
6a
Kirsch P.
Modern
Organofluorine Chemistry
Wiley-VCH;
Weinheim:
2004.
6b
Bégué J.-P.
Bonnet-Delpon D.
Bioorganic and Medicinal Chemistry of Fluorine
John Wiley & Sons;
Hoboken / NJ:
2008.
6c
Fluorine in Medicinal
Chemistry and Chemical Biology
Ojima I.
Wiley-Blackwell;
Chichester:
2009.
7
Romanenko VD.
Kukhar VP.
Chem. Rev.
2006,
106:
3868
8a
Quin LD.
A
Guide to Organophosphorus Chemistry
Wiley;
New
York:
2000.
8b
Savignac P.
Iorga B.
Modern Phosphonate
Chemistry
CRC Press;
Boca Raton / FL:
2003.
8c
Atmani A.
Memmou F.
Bouillon J.-Ph.
C.
R. Chim.
2009,
12:
963
8d
Albrecht Ł.
Albrecht A.
Krawczyk H.
Jørgensen KA.
Chem.
Eur. J.
2010,
16:
28
8e
Enders D.
Saint-Dizier A.
Lannou M.-I.
Lenzen A.
Eur. J. Org. Chem.
2006,
29
9a
Samanta S.
Zhao C.-G.
J.
Am. Chem. Soc.
2006,
128:
7442
9b
Samanta S.
Perera S.
Zhao C.-G.
J.
Org. Chem.
2010,
75:
1101
9c
Dodda R.
Zhao C.-G.
Org. Lett.
2006,
8:
4911
10a
Schoth R.-M.
Sevenard D.
Pashkevich K.
Röschenthaler G.-V.
Coord. Chem. Rev.
2000,
210:
101
10b
Sevenard DV.
Lork E.
Pashkevich KI.
Röschenthaler G.-V.
Heteroat.
Chem.
2002,
13:
97
10c Chizhov, D. L.; Slepukhin,
P. A.; Charushin, V. N.; Röschenthaler G.-V. J. Fluorine Chem., submitted.
11
Francke R.
Röschenthaler G.-V.
Chemiker-Ztg.
1989,
113:
115
12a
Chizhov DL.
Ratner VG.
Pashkevich KI.
Russ. Chem.
Bull.
1999,
48:
758
12b
Yachevskii DS.
Chizhov DL.
Ratner VG.
Pashkevich KI.
Russ.
Chem. Bull., Int. Ed.
2001,
50:
1233
12c
Chizhov DL.
Pashkevich KI.
Röschenthaler G.-V.
J. Fluorine Chem.
2003,
123:
267
12d
Chizhov DL.
Röschenthaler G.-V.
J.
Fluorine Chem.
2006,
127:
235
12e
Sevenard DV.
Kazakova O.
Schoth R.-M.
Lork E.
Chizhov DL.
Poveleit J.
Röschenthaler G.-V.
Synthesis
2008,
1867
13
Typical Procedure
for the Preparation of Compounds 4-7
A mixture
of diketone 3 (10.0 mmol), phosphorus reagent [11.0
mmol in the case of diethyl phosphite or ethyl(methyl)phosphonite,
15 mmol in the case of ethyl(phenyl)phosphonite, or 20 mmol in the
case of diphenylphosphine oxide], and triethylborate (1.60
g, 11.0 mmol in the case of phosphite and phosphonites or 2.92 g, 20.0
mmol in the case of diphenylphosphine oxide) was refluxed in MeCN
(20 mL) for the respective time (Table
[¹]
). All volatile materials
were removed in vacuo, and the residue was dissolved in Et2O
(30 mL). The ether solution was washed with H2O (10 mL)
and 10% solution of Na2CO3 (3 × 10
mL). For compounds 6 and 7 a
sat. solution of NaHCO3 was used. Et2O was
removed, the crude product was dissolved in CHCl3 (10
mL) and filtered through a layer of silica (3 sm). The solvent was
evaporated, and the residue was dried in vacuo for 12 h. For compounds 6 and 7, the products
were purified by column chromatography (EtOAc-hexane = 1:2).
Data for Diethyl 1-Hydroxy-3-(4-nitrophenyl)-3-oxo-1-(trifluoromethyl)propylphosphonate (4b)
Yellowish viscous oil. ¹H
NMR (200 MHz, CDCl3): δ = 1.23 (t,
3 H, Me, J = 7.1
Hz), 1.27 (t, 3 H, Me, J = 7.1
Hz), 3.21 (dd, 1 H, J
Ha-Hb = 16.1
Hz, J
Ha-P = 18.6
Hz, CHH), 3.82 (dd, 1 H, J
Ha-Hb = 16.1
Hz, J
Hb-P = 7.3
Hz, CHH), 4.10-4.36 (m, 4 H,
2 OCH2), 6.74 (d, 1 H, J
H-P = 8.3
Hz, OH) 7.61-7.66 (m, 2 H, Ar), 7.88-7.93 (m,
2 H, Ar). ¹9F NMR (188 MHz, CDCl3,
C6F6): δ = 88.96
(d, J
F-P = 5.2
Hz, CF3). ³¹P-¹H decoupled
(81 MHz, CDCl3, 85% H3PO4): δ = 16.68
(q,
J
P-F = 5.2
Hz). ¹³C NMR (50 MHz, CDCl3) δ = 16.13
(d,
³
J
C-P = 5.2
Hz, Me), 38.64 (s, CH2), 63.58 (d, ²
J
C-P = 7.4
Hz, OCH2), 63.63 (d, ²
J
C-P = 7.4
Hz, OCH2), 75.58 (dq,
¹
J
C-P = 164.6
Hz, ²
J
C-F = 29.0
Hz), 124.41 (qd, CF3, ¹
J
C-F = 285.4
Hz, ²
J
C-P = 12.6
Hz), 124.42, (CH, Ar), 130.87 (CH, Ar), 143.03 (Ar), 150.70 (Ar),
195.94 (d, ³
J
C-P = 8.5 Hz,
C=O). Anal. Calcd for C14H17NPF3O7:
C, 42.12; H, 4.29; F, 14.28. Found: C, 42.31; H, 4.17; F, 14.42.
14
Singh YP.
Saxena S.
Rai AK.
Synth.
React. Inorg. Met.-Org. Chem.
1982,
12:
867
15a
Jullien J.
Pechine JM.
Perez F.
Piade JJ.
Tetrahedron
1982,
38:
1413
15b
Pavlov AM.
Chizhov DL.
Charushin VN.
Russ. J. Org. Chem.
2005,
41:
1449
15c
Bonacorso HG.
Martins MAP.
Bittencourt SRT.
Lourega RV.
Zanatta N.
Flores AFC.
J. Fluorine Chem.
1999,
99:
177
15d
Mkrtchyan EG.
Yachevskii DS.
Chizhov DL.
Charushin VN.
Russ.
Chem. Bull.
2005,
54:
2150
16a
Mikhailov BM.
Pure Appl. Chem.
1977,
49:
749
16b Kunstle G, and Siegel H. inventors; DE 2402426.
; Chem. Abstr. 1975, 83, 193406
16c
Balaban AT.
Rentea CN.
Mocanu M.
Tetrahedron Lett.
1964,
5:
2049
16d
Chaturvedi A.
Nagar PN.
Srivastava G.
Synth.
React. Inorg. Met.-Org. Chem.
1993,
23:
1599
17
Pashkevich KI.
Filyakova VI.
Ratner VG.
Khomutov OG.
Russ.
Chem. Bull.
1998,
47:
1239 ;
and references cited therein
18
General Procedure
for the Preparation of Compounds 8-10
To
a vigorously stirred solution of phosphonate 4 or phosphinate 5 or 6 (5.0 mmol)
and dry pyridine (0.79 g, 10 mmol) in dry CH2Cl2 (20
mL) a solution of TFAA (2.10 g, 10 mmol) in dry CH2Cl2 (20
mL) was added dropwise at 0 ˚C. The reaction mixture was
stirred for 4 h at the same temperature, warmed to r.t., washed
with cold H2O (ca. 5 ˚C, 3 × 10
mL), and filtered through layer of silica (4 sm). The solvent was
evaporated and residue was dried in vacuo for 12 h.
Data for Diethyl 3-(4-Nitrophenyl)-3-oxo-1-(trifluoromethyl)prop-1-enylphosphonate (8b)
Yellow viscous oil; E/Z = 10:1.
Compound (
Z
)-8b: ¹H NMR (200 MHz,
CDCl3): δ = 1.27
(t, 6 H, 2 Me, J = 7.1
Hz), 4.01-4.17 (m, 4 H, 2 OCH2), 7.57 (dq, 1
H, J
H-P = 39.0
Hz, J
H-F = 1.5
Hz, =CH), 8.02-8.06 (m, 2 H, Ar), 8.31-8.36
(m, 2 H, Ar). ¹9F NMR (188 MHz, CDCl3,
C6F6): δ = 99.27
(s). ³¹P-¹H
coupled (81 MHz, CDCl3, 85% H3PO4): δ = 6.67
(dm, J
P-H = 39.0
Hz). ³¹P-¹H decoupled
(81 MHz, CDCl3, 85% H3PO4): δ = 6.67
(q,
J
P-F = 2.5
Hz). ¹³C NMR (50 MHz, CDCl3): δ = 16.00
(d, ³
J
C-P = 7.1
Hz, Me), 63.80 (d, ²
J
C-P = 5.7
Hz, OCH2), 121.65 (qd, CF3, ¹
J
C-F = 275.5
Hz, ²
J
C-P = 15.5
Hz), 124.06 (CH, Ar), 129.00 (dq, ¹
J
C-P = 182.3
Hz, ²
J
C-F = 32.5
Hz), 129.82, (CH, Ar), 139.48 (Ar), 147.39 (m, =CH), 150.82
(Ar), 190.20 (d, ³
J
C-P = 7.1
Hz, C=O).
Compound (
E
)-8b: ¹H
NMR (200 MHz, CDCl3): δ = 1.41
(t, 6 H, 2 Me, J = 7.1
Hz), 4.19-4.35 (m, 4 H, 2 OCH2), 7.77 (d, 1
H, J
H-P = 24.0
Hz, =CH), 8.02-8.06 (m, 2 H, Ar), 8.31-8.36
(m, 2 H, Ar). ¹9F NMR (188 MHz, CDCl3,
C6F6): δ = 104.36
(d, J
F-P = 5.5
Hz). ³¹P-¹H
decoupled (81 MHz, CDCl3, 85% H3PO4): δ = 9.06
(q, J
P-F = 5.2
Hz). ¹³C NMR (50 MHz, CDCl3): δ = 16.20
(d, ³
J
C-P = 7.0
Hz, Me), 64.09 (d, ²
J
C-P = 5.7
Hz, OCH2), 124.26 (CH, Ar), 130.04, (CH, Ar), 148.66
(m, =CH). Signals of carbon without hydrogen were not found.
Anal. Calcd for C14H15NPF3O6:
C, 44.11; H, 3.97; F, 14.95. Found: C, 44.03; H, 3.75; F, 15.10.
19
Nenajdenko VG.
Druzhinin SV.
Balenkova ES.
Chemistry of α,β-Unsaturated
Trifluoromethyl Ketones
Nova Sci. Publ.;
New
York:
2007.
20
Dembitsky VM.
Al Quntar AAA.
Haj-Yehiaa A.
Srebnik M.
Mini-Rev.
Org. Chem.
2005,
2:
91
21a
Kenyon GL.
Westheimer FN.
J. Am. Chem. Soc.
1966,
88:
3557
21b
Costisella B.
Keitel I.
Gross H.
Tetrahedron
1981,
37:
1227