References
1 For a review, see: Royles BJL.
Chem. Rev.
1995,
95:
1981
2
Palk S.
Carmeli S.
Cullingham J.
Moore RE.
Patterson GML.
Tius MA.
J. Am. Chem. Soc.
1994,
116:
8116
3
Unson MD.
Rose CB.
Faulkner DJ.
J. Org. Chem.
1993,
58:
6336
4
Pettit GR.
Camano Y.
Dufresne C.
Cerny RL.
Herald CL.
Schmidt JM.
J. Org. Chem.
1989,
54:
6005
5
Wood JL.
Petsch DT.
Stoltz BM.
Hawkins EM.
Elbaum D.
Stover DR.
Synthesis
1999,
1529
6a
Fehrentz JA.
Bourdel E.
Califano JC.
Chaloin O.
Devin C.
Garrouste P.
Lima-Leite AC.
Llinares M.
Rieunier F.
Vizavonna J.
Winternitz F.
Loffet A.
Martinez J.
Tetrahedron Lett.
1994,
35:
1557
6b
Schmidt U.
Ridel B.
Haas G.
Griesser H.
Vetter A.
Weinbrenner S.
Synthesis
1993,
216
6c
Klutchko S.
O’Brien P.
Hodges JC.
Synth. Commun.
1989,
19:
2573
7
Huang P.-Q.
Wu T.-J.
Ruan Y.-P.
Org. Lett.
2003,
5:
4341
8
Hunter R.
Richards P.
Synlett
2003,
271
9a
Detsi A.
Micha-Screttas M.
Igglessi-Markopoulou O.
J. Chem. Soc., Perkin Trans. 1
1998,
2443
9b
Jones RCF.
Begley MJ.
Peterson GE.
Sumaria S.
J. Chem. Soc., Perkin Trans. 1
1990,
1959
9c
Hori K.
Arai M.
Nomura K.
Yoshii E.
Chem. Pharm. Bull.
1987,
33:
4368
9d
Jones RCF.
Peterson GE.
Tetrahedron Lett.
1983,
24:
4751
9e
Jones RCF.
Peterson GE.
Tetrahedron Lett.
1983,
24:
4755
9f
Jones RCF.
Peterson GE.
Tetrahedron Lett.
1983,
24:
4757
9g
Jones RCF.
Sumaria S.
Tetrahedron Lett.
1978,
3173
10a
Jouin P.
Castro B.
J. Chem. Soc., Perkin Trans. 1
1987,
1177
10b
Liu ZX.
Ruan XX.
Huang X.
Bioorg. Med. Chem. Lett.
2003,
13:
2505
For other approaches to optically active tetramic acids and derivatives, see:
11a ref. 7.
11b
Fustero S.
Torre MG.
Danz-Cervera JF.
Arellano CR.
Piera J.
Simon A.
Org. Lett.
2002,
4:
3651
11c
Banziger M.
McGarrity JF.
Meul T.
J. Org. Chem.
1993,
58:
4010
12
Poncet J.
Jouin P.
Castro B.
J. Chem. Soc., Perkin Trans. 1
1990,
611
13a
Pettic GR.
Thornton TJ.
Mullaney JT.
Boyd MR.
Herald DL.
Singh S.-B.
Flahive EJ.
Tetrahedron
1994,
50:
12097
13b
Pettit GR.
Herald DL.
Singh
S.-B.
Thornton TJ.
Mullaney JT.
J. Am. Chem. Soc.
1991,
113:
6692
14
Akaji K.
Hayashi Y.
Kiso Y.
Kuriyama N.
J. Org. Chem.
1999,
64:
405
15 For a direct racemic approach to methyl 5-iso-propyl tetramate, see: Williard PG.
de Laszlo SE.
J. Org. Chem.
1984,
49:
3489
For reviews on the use of (R)-phenylglycinol and other β-amino alcohols as chiral auxiliaries, see:
16a
Husson H.-P.
Royer J.
Chem. Soc. Rev.
1999,
28:
383
16b
Groaning MD.
Meyers AI.
Tetrahedron
2000,
56:
9843
16c
Ager DJ.
Prakash I.
Schaad DR.
Chem. Rev.
1996,
96:
835
16d
Sardina FJ.
Rapoport H.
Chem. Rev.
1996,
96:
1825
17
Baussanne I.
Chiaroni A.
Husson HP.
Riche C.
Royer J.
Tetrahedron Lett.
1994,
35:
3931
18a
Dudot B.
Chiaroni A.
Royer J.
Tetrahedron Lett.
2000,
41:
6355
18b
Dudot B.
Royer J.
Sevrin M.
George P.
Tetrahedron Lett.
2000,
41:
4367
18c
Dudot B.
Micouin L.
Baussanne I.
Royer J.
Synthesis
1999,
688
18d
Poli G.
Baffoni SC.
Giambastiani G.
Reginato G.
Tetrahedron
1998,
54:
10403
18e
Baussanne I.
Schwardt O.
Royer J.
Tetrahedron Lett.
1997,
38:
2259
18f
Baussanne I.
Royer J.
Tetrahedron Lett.
1996,
37:
1213
For reviews, see:
19a
Rassu G.
Zanardi F.
Battistini L.
Casiraghi G.
Chem. Soc. Rev.
2000,
29:
109
19b
Casiraghi G.
Zanardi F.
Chem. Rev.
1995,
95:
1677
19c
Casiraghi G.
Rassu G.
Synthesis
1995,
607
20
Lautens M.
Han W.
Liu JHC.
J. Am. Chem. Soc.
2003,
125:
4028
21a
Paintner FF.
Metz M.
Bauschke G.
Synlett
2003,
627
21b
James GD.
Mills SD.
Pattenden G.
J. Chem. Soc., Perkin Trans. 1
1993,
2567
21c
Jones RCF.
Patience JM.
J. Chem. Soc., Perkin Trans. 1
1990,
2350
21d
Jones RCF.
Bates AD.
Tetrahedron Lett.
1986,
27:
5285
22a
Paintner FF.
Metz M.
Baoschke G.
Synthesis
2003,
869
22b
Duc L.
McGarrity JF.
Meul T.
Warm A.
Synthesis
1992,
391
22c
Laffan DDP.
Panziger M.
Duc L.
Evans AR.
McGarrity JF.
Meul T.
Helv. Chim. Acta
1992,
75:
892
22d
Kochhar KS.
Carson HJ.
Clouser KA.
Elling JW.
Gramens LA.
Parry JL.
Sherman HL.
Braat K.
Pinnick HW.
Tetrahedron Lett.
1984,
25:
1871
23
Representative Procedure for the Alkylation of (
R
)-7/8: To a solution of (R)-7 (104 mg, 0.42 mmol) in THF (8.4 mL, containing 0.37 mL of HMPA as a co-solvent) was added dropwise t-BuLi (0.67 mL, 1.5 M in pentane) at -78 ºC. After being stirred for 1 h, MeI (0.08 mL, 1.26 mmol) was added and the stirring continued for an additional 6 h at the same temperature. The reaction was quenched by sat. NH4Cl. The resulting mixture was extracted with Et2O, and the organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel to give 9b (62 mg, colorless oil), its diastereomer (7 mg, pale yellow oil) (combined yield, 63%) and recovered 7 (7 mg, yield based on the recovered starting material, 68%). Compound 9b: [α]D
20 +19.4 (c 1.1, CHCl3). IR (KBr): 3374, 2981, 2934, 1657, 1625, 1340, 1221, 1029 cm-1. 1H NMR (500 MHz, CDCl3): δ = 7.40-7.20 (m, 5 H, ArH), 5.18 (dd, J = 6.4, 7.7 Hz, 1 H, D2O exchangeable, OH), 5.01 (s, 1 H, O=CCH=), 4.51 (dd, J = 3.1, 7.7 Hz, 1 H, PhCHN), 4.27 (ddd, J = 7.7, 7.7, 12.3 Hz, 1 H, HOCH
2), 4.00 (m, 3 H, CH3CH
2O and HOCH
2), 3.73 (q, J = 6.8 Hz, 1 H, CH3CHN), 1.37 (t, J = 7.1 Hz, 3 H, CH
3CH2O), 1.28 (d, J = 6.8 Hz, 3 H, CH
3CHN) ppm. 13C NMR (125 MHz, CDCl3): δ = 176.42, 173.18, 138.34, 128.80 (2 C), 127.77, 127.05 (2 C), 93.35, 67.10, 64.91, 61.90, 57.17, 15.83, 14.06 ppm. MS (ESI):
m/z (%) = 262 (13) [M + H+], 244 (5) [M + H+ - H2O], 142 (100). HRMS calcd for [C15H19NO3 + H]+: 262.1438. Found: 262.1440. Minor diastereomer of 9b: [α]D
20 +17.1 (c 1.1, CHCl3). IR (KBr): 3367, 2981, 2932, 1659, 1625, 1340, 1222, 1029 cm-1. 1H NMR (500 MHz, CDCl3): δ = 7.40-7.20 (m, 5 H, ArH), 5.02 (s, 1 H, =CHC=O), 4.82 (dd, J = 3.8, 7.5 Hz, PhCHN), 4.21 (m, 1 H, HOCH
2N), 4.09 (m, 2 H, HOCH
2 and OH), 3.98 (m, 2 H, CH3CH
2O), 3.88 (q, J = 6.8 Hz, 1 H, CH3CHN), 1.37 (t, J = 7.1 Hz, 3 H, CH
3CH2O), 1.14 (d, J = 6.8 Hz, 3 H, CH
3CHN). MS (ESI): m/z (%) = 262 (100) [M + H+]. HRMS calcd for [C15H19NO3 + H]+: 262.1438. Found: 262.1432.
24a
Courcambeck J.
Bihel F.
Michelis C.
Quelever G.
Kraus JL.
J. Chem. Soc., Perkin Trans. 1
2001,
1421
24b
Bach T.
Brummerhop H.
Harms K.
Chem.-Eur. J.
2000,
6:
3838
25a
Huang PQ.
Wang SL.
Ye JL.
Ruan YP.
Huang YQ.
Zheng H.
Gao JX.
Tetrahedron
1998,
54:
12547
25b
Bernardi A.
Micheli F.
Potenza D.
Scolastico C.
Villa R.
Tetrahedron Lett.
1990,
31:
4949
26a
Collum DB.
Kahne D.
Gut SA.
DePue RT.
Mohamadi F.
Wanat RA.
Clardy J.
VanDuyne G.
J. Am. Chem. Soc.
1984,
106:
4865
26b
Castonguay LA.
Guiles JW.
Rappe AK.
Meyers AI.
J. Org. Chem.
1992,
57:
3819
26c
Haeffner F.
Brandt PR.
Gawley E.
Org. Lett.
2002,
4:
2101