Supporting information for Titanium isopropoxide as efficient catalyst for… S1
Balan, D.; Adolfsson, H.
Titanium isopropoxide as efficient catalyst for the aza-
Baylis-Hillman reaction. Selective formation of α-
methylene-β-amino acid derivatives
Daniela Balan and Hans Adolfsson*
Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden
hansa@organ.su.se
Supporting Information
Characterization data for the compounds in Table 2 (melting points are uncorrected).
Methyl α-methylene-β-[(p-toluenesulfonyl)amino]-3-(2-furanyl)propionate (3a). Mp 91-
92 °C;
1
H-NMR (400 MHz, CDCl
3
) δ 2.40 (s, 3H), 3.67 (s, 3H), 5.38 (d, J = 9.3 Hz, 1H), 5.65
(d, J = 9.3 Hz, 1H), 5.84 (s, 1H), 6.05 (dt, J = 3.3 and 0.9 Hz, 1H), 6.21 (dd, J = 3.3 and 1.8
Hz, 1H), 6.23 (s, 1H), 7.21 (dd, J = 1.8 and 0.9 Hz, 1H), 7.24 (d, J = 8.4 Hz, 2H), 7.68 (d, J =
8.4 Hz, 2H);
13
C-NMR (100 MHz, CDCl
3
) δ 21.73, 52.31, 53.82, 107.64, 110.77, 127.41,
128.59, 129.68, 137.07, 137.76, 142.50, 143.61, 151.41, 165.79; MS (MALDI-TOF) (m/z)
373.943 (MK
+
) 357.987 (MNa
+
). Anal. Calcd for C
16
H
17
NO
5
S: C, 57.30; H, 5.11; N, 4.18.
Found: C, 56.97; H, 5.05; N, 4.07.
Methyl α-methylene-β-[(p-toluenesulfonyl)amino]-3-(2-pyridyl)propionate (3b). Work-up
as reported for 1 followed by a short column on silica gel to separate the product from the
alcohol adduct. Eluent pentane:ethyl acetate 2:1, R
f
0.25 Mp 85-86 °C;
1
H-NMR (400 MHz,
CDCl
3
) δ 2.36 (s, 3H), 3.64 (s, 3H), 5.38 (d, J = 8.0 Hz, 1H), 5.87 (s, 1H), 6.25 (s, 1H), 6.51
(d, J = 8.1 Hz, 1H), 7.11 (ddd, J = 7.5, 4.9 and 1.2 Hz, 1H), 7.18 (d, J = 7.8 Hz, 2H), 7.25 (d,
J = 8.1 Hz, 1H), 7.54 (dt, J = 7.7 and 1.8 Hz, 1H), 7.66 (d, J = 8.4 Hz, 2H), 8.43 (ddd, J = 4.8,
1.8 and 1.0 Hz, 1H);
13
C-NMR (100 MHz, CDCl
3
) δ 21.63, 52.12, 58.57, 122.20, 122.73,
127.38, 128.37, 129.56, 136.85, 137.59, 139.05, 143.39, 148.93, 157.09, 166.06; MS
(MALDI-TOF) (m/z) 385.059 (MK
+
) 369.073 (MNa
+
) 347.090 (MH
+
). Anal. Calcd for
C
17
H
18
N
2
O
4
S: C, 58.94; H, 5.24; N, 8.09. Found: C, 58.76; H, 5.24; N, 7.96.
Methyl α-methylene-β-[(p-toluenesulfonyl)amino]-3-(3-chlorophenyl)propionate (3c).
Work-up as reported for 1 followed by a short column on silica gel to separate the product