References and Notes
1
Hashimoto K.
Ohfune Y.
Shirahama H.
Tetrahedron Lett.
1995,
36:
6235
2
Jao E.
Bogen S.
Saksena AK.
Girijavallabhan V.
Tetrahedron Lett.
2003,
44:
5033
3
Jiang B.
Xu M.
Angew. Chem. Int. Ed.
2004,
43:
2543
4a
Cossy J.
Cases M.
Pardo DG.
Synlett
1998,
507
4b
Collado I.
Ezquerra J.
Mateo AI.
Rubio A.
J. Org. Chem.
1998,
63:
1995
4c
Collado I.
Ezquerra J.
Mateo AI.
Pedregal C.
Rubio A.
J.
Org. Chem.
1999,
64:
4304
5
Huck BR.
Llamas L.
Robarge MJ.
Dent TC.
Song J.
Hodnick WF.
Crumrine C.
Stricker-Krongrad A.
Harrington J.
Brunden KR.
Bennani YL.
Bioorg. Med. Chem. Lett.
2006,
16:
4130
6
Santora VJ.
Covel JA.
Hayashi R.
Hofilena BJ.
Ibarra JB.
Pulley MD.
Weinhouse MI.
Sengupta D.
Duffield JJ.
Semple G.
Webb RR.
Sage C.
Ren A.
Pereira G.
Knudsen J.
Edwards JE.
Suarez M.
Frazer J.
Thomsen W.
Hauser E.
Whelan K.
Grottick AJ.
Bioorg.
Med. Chem. Lett.
2008,
18:
1490
7
Heath P.
Roberts E.
Wessel HP.
Workman JA.
Sweeney JB.
J. Org. Chem.
2003,
68:
4083
8 Related aza-Claisen rearrangements: Chao S.
Kunng
F.-A.
Gu J.-M.
Ammon HL.
Mariano PS.
J. Org. Chem.
1984,
49:
2708
9a
Larson SD.
Grieco PA.
J. Am. Chem. Soc.
1985,
107:
1768
9b
Fray AH.
Augeri DJ.
Kleinman EF.
J. Org. Chem.
1988,
53:
896
10
Roberts E.
Sançon J.
Workman JA.
Sweeney JB.
Org. Lett.
2003,
5:
4775
11
Key Data for 4
¹H
NMR (400 MHz, CDCl3): δ = 1.24-1.31
(6 H, m), 2.33-2.38 (1 H, br m), 2.41 (3 H, s), 2.67-2.74
(1 H, m), 2.82 (1 H, dd, J = 8.5,
9.0 Hz), 2.90-2.97 (2 H, m), 3.80-3.88 (1 H, m),
4.18-4.31 (4 H, m), 5.31-5.34 (1 H, m), 5.83-5.86
(1 H, m). ¹³C NMR (100 MHz, CDCl3): δ = 14.3,
14.4, 37.2, 37.4, 41.7, 58.3, 60.8, 61.0, 63.0, 78.0, 128.1, 134.8,
168.0 (C=O), 169.4. MS (ES+): m/z calcd for C14H21NO4:
268.1543; found: 268.1539.
12
Key Data for 5
¹H
NMR (250 MHz, CDCl3): δ = 1.27 (6 H,
t, J = 7.1 Hz), 1.60 (1 H, d, J = 10.8 Hz), 1.79-1.86
(1 H, m), 2.50 (3 H, s), 2.51-2.58 (2 H, m), 2.69 (1 H,
dd, J = 8.5, 9.0 Hz), 3.01 (1 H,
br dd, J = 2.5, 5.1 Hz), 4.11-4.23
(4 H, m), 6.05-6.17 (1 H, m). ¹³C
NMR (62.5 MHz, CDCl3): δ = 14.5, 14.6,
39.4, 39.5, 40.7, 45.7, 51.1, 61.1, 62.0, 73.1, 133.2, 136.1, 170.5, 171.2.
MS (ES+): m/z calcd
for C14H21NO4: 268.1543; found: 268.1543.
13
Mageswaran S.
Ollis WD.
Sutherland IO.
J. Chem. Soc., Perkin Trans. 1
1981,
1953
14
Key Data for 7
¹H
NMR (400 MHz, CDCl3): δ = 2.28 (3 H,
s), 2.28-2.35 (1 H, m), 2.35-2.41 (1 H, m), 2.60-2.70
(1 H, m), 2.75-2.85 (1 H, m), 2.90 (1 H, d), 2.90 (1 H,
d), 3.50-3.57 (1 H, br m), 3.70 (3 H, s), 5.20-5.28
(1 H, m), 5.73-5.81 (1 H, m). ¹³C NMR
(100 MHz, CDCl3): δ = 39.0, 41.3, 42.6,
52.4, 55.1, 65.2, 72.3, 128.8 , 135.5, 172.3 MS (CI+): m/z (%) = 182 (100) [MH+],
122 (75), 79 and 49. HRMS: m/z calcd
for C10H15NO2: 182.1182; found:
182.1181.
15 The relative stereochemistry of 7 was deduced from NOE experiments, which
will be reported elsewhere in due course.
