C
Synlett
A. H. Aldmairi et al.
Letter
was filtered and washed with CH Cl (2 × 10 mL). The combined
2-Isopropyl-3-tosyloctahydrobenzo[d]oxazole (6e)
2
2
1
organic layers were concentrated in vacuo and purified by
column chromatography on silica gel to afford the oxazolidine
as a clear oil.
H NMR (300 MHz, CDCl ): δ = 7.70 (d, J = 8.0, 2 H), 7.36 (d, J =
3
8.0, 2 H), 4.70 (d, J = 3.8 Hz, 1 H), 3.51 (ddd, J = 11.5, 10.6, 3.7 Hz,
5 H), 2.46 (s, 3 H), 2.35 (ddd, J = 11.5, 9.7, 3.7 Hz, 1 H), 2.32–2.23
(m, 1 H), 2.07–1.97 (m, 1 H), 1.85–1.73 (m, 2 H), 1.55–1.40 (m, 1
H), 1.24–1.13 (m, 4 H), 1.06 (d, J = 6.9 Hz, 3 H), 1.01 (d, J = 6.9 Hz,
2
-Isopropyl-3-tosyloxazolidine (6a)
1
H NMR (500 MHz, CDCl ): δ = 7.67 (d, J = 7.6 Hz, 2 H), 7.26 (d,
3
13
J = 7.6 Hz, 2 H), 4.85 (d, J = 5.5 Hz, 1 H), 3.71 (ddd, J = 8.0, 6.9, 3.4
Hz, 1 H), 3.54 (ddd, J = 11.6, 6.8, 3.4 Hz, 1 H), 3.27 (ddd, J = 11.6,
3 H). C NMR (101 MHz, CDCl ): δ = 144.0, 132.1, 129.9 (2 C),
3
128.3 (2 C), 95.8, 81.4, 65.0, 33.8, 29.5 (2 C), 23.8, 23.2, 21.5,
–1
8
.6, 6.9 Hz, 1 H), 3.06 (td, J = 8.3, 6.9 Hz, 1 H), 2.36 (s, 3 H), 1.96–
18.9, 16.1. IR (neat): ν = 2941, 2874, 1458, 1350, 1109 cm
.
13
+
1.78 (m, 1 H), 0.93 (d, J = 6.1 Hz, 3 H), 0.88 (d, J = 6.7 Hz, 3 H).
C
HRMS (APCI): m/z calcd for C17H26NO S [M + H] : 324.1633;
3
NMR (75 MHz, CDCl ): δ = 144.1, 134.8, 129.9 (2 C), 127.8 (2 C),
found: 324.1617.
3
9
5.85, 65.2, 46.8, 33.0, 21.6, 18.2, 16.3. IR (neat): ν = 2965, 2875,
2-Cyclohexyl-3-tosyloxazolidine (6f)
–1
1
1470, 1346, 1092 cm . HRMS (APCI): m/z calcd for C13H20NO3S
H NMR (400 MHz, CDCl ): δ = 7.67 (d, J = 8.1 Hz, 2 H), 7.28 (d,
3
+
[
M + H] : 270.1164; found: 270.1151.
J = 8.1 Hz, 2 H), 4.88 (d, J = 6.0 Hz, 1 H), 3.69 (td, J = 7.5, 3.6 Hz, 1
H), 3.56–3.49 (m, 1 H), 3.31–3.22 (m, 1 H), 3.05 (ddd, J = 15.5,
8.1, 6.6 Hz, 1 H), 2.36 (s, 3 H), 1.80–1.65 (m, 4 H), 1.62–1.55 (m,
4
-Ethyl-2-isopropyl-3-tosyloxazolidine (6c)
1
Major isomer: H NMR (400 MHz, CDCl ): δ = 7.74 (d, J = 8.3 Hz,
2
3
13
H), 7.35 (d, J = 8.3 Hz, 2 H), 4.76 (d, J = 6.1 Hz, 1 H), 3.61–3.54
1 H), 1.20–1.07 (m, 3 H), 1.07–0.95 (m, 3 H). C NMR (126 MHz,
(m, 2 H), 3.11–2.94 (m, 1 H), 2.45 (s, 3 H), 2.10–2.00 (m, 1 H),
CDCl ): δ = 144.0, 134.8, 130.0 (2 C), 127.9 (2 C), 95.2, 65.7, 48.1,
3
1
.87–1.74 (m, 1 H), 1.62–1.51 (m, 1 H), 1.07 (d, J = 7.0 Hz, 3 H),
42.4, 28.6, 27.0, 26.3, 25.9, 25.7, 21.6. IR (neat): ν = 2926, 2855,
13
–1
0.99 (t, J = 7.2 Hz, 3 H), 0.94 (d, J = 7.0 Hz, 3 H). C NMR (101
1450, 1350, 1090 cm . HRMS (APCI): m/z calcd for C15H24NO3S
+
MHz, CDCl ): δ = 144.6, 134.5, 129.8 (2 C), 128.0 (2 C), 96.9,
[M + H] : 310.1477; found: 310.1477.
3
1
69.6, 60.8, 32.5, 21.6, 18.7, 16.4, 10.6. Minor isomer: H NMR
(11) Synthesis of 1a and 1b: (a) Ye, W.; Leow, D.; Goh, S. L. M.; Tan,
C.; Chian, C.; Tan, C. Tetrahedron Lett. 2006, 47, 1007. Synthesis
of 1c: (b) Ando, T.; Kano, D.; Minakata, S.; Ryu, I.; Komatsu, M.
Tetrahedron 1998, 54, 13485. Synthesis of 1d: (c) Kano, D.;
Minakata, S.; Komatsu, M. J. Chem. Soc., Perkin Trans. 1 2001,
3186. Synthesis of 2b: (d) Trost, B. M.; King, S. A. J. Am. Chem.
Soc. 1990, 112, 408. Synthesis of 2d: (e) Hazelden, I. R.; Ma, X.;
Langer, T.; Bower, J. F. Angew. Chem. Int. Ed. 2016, 55, 11198.
(
400 MHz, CDCl ): δ = 4.94 (d, J = 4.4 Hz, 1 H), 3.40–3.30 (m, 2
3
H), 2.93–2.87 (m, 1 H), 2.45 (s, 3 H), 2.05–1.95 (m, 1 H), 1.45–
1
0
1
.35 (m, 1 H), 1.01 (d, J = 6.9 Hz, 3 H), 0.95 (d, J = 6.9 Hz, 3 H),
.82 (t, 6.7 Hz, 3 H). C NMR (101 MHz, CDCl ): δ = 144.0, 135.1,
29.9 (2 C), 127.7 (2 C), 95.4, 50.7, 33.7, 25.8, 18.0, 16.7, 15.5. IR
13
3
–1
(neat): ν = 2965, 2875, 2153, 1350, 1092 cm . HRMS (APCI):
+
m/z calcd for C15H24NO S [M + H] : 298.1477; found: 298.1466.
3
©
Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–C