1884
E. Tayama, S. Saito
Letter
Synlett
7950. (e) Tayama, E.; Sugai, S. Tetrahedron Lett. 2007, 48, 6163.
(f) Tayama, E.; Sugai, S.; Hara, M. Tetrahedron Lett. 2006, 47,
7533. (g) Tayama, E.; Sugai, S. Synlett 2006, 849.
(14) When the reaction was carried out at 0 °C, (Z)-3aa and 4aa
were obtained in 7% combined yield [(E)-3aa/(Z)-3aa/4aa =
0:51:49] with the recovery of the substrates [(Z)-1a, 84%; 2a,
86%].
(8) Tayama, E.; Horikawa, K.; Iwamoto, H.; Hasegawa, E. Tetrahe-
dron Lett. 2014, 55, 3041.
(15) Representative Procedure
(9) Preparation of 1-amino-2-vinyl (alkenyl) cyclopropanes: (a) de
Meijere, A.; Chaplinski, V.; Winsel, H.; Kordes, M.; Stecker, B.;
Gazizova, V.; Savchenko, A. I.; Boese, R.; Schill, F. Chem. Eur. J.
2010, 16, 13862. (b) Wiedemann, S.; Rauch, K.; Savchenko, A.;
Marek, I.; de Meijere, A. Eur. J. Org. Chem. 2004, 631.
(c) Williams, C. M.; Chaplinski, V.; Schreiner, P. R.; de Meijere, A.
Tetrahedron Lett. 1998, 39, 7695.
(10) Representative examples of preparation of 1-amino-2-vinylcy-
clopropane-1-carboxylic acid derivatives: (a) Lou, S.; Cuniere,
N.; Su, B.-N.; Hobson, L. A. Org. Biomol. Chem. 2013, 11, 6796.
(b) Tang, W.; Wei, X.; Yee, N. K.; Patel, N.; Lee, H.; Savoie, J.;
Senanayake, C. H. Org. Process Res. Dev. 2011, 15, 1207.
(c) Crane, Z. D.; Nichols, P. J.; Sammakia, T.; Stengel, P. J. J. Org.
Chem. 2011, 76, 277.
(11) Preparation of 1-oxy-2-vinyl (alkenyl) cyclopropanes:
(a) McGaffin, G.; Grimm, B.; Heinecke, U.; Michaelsen, H.; de
Meijere, A.; Walsh, R. Eur. J. Org. Chem. 2001, 3559. (b) Militzer,
H.-C.; Schömenauer, S.; Otte, C.; Puls, C.; Hain, J.; Bräse, S.; de
Meijere, A. Synthesis 1993, 998. (c) Davies, H. M. L.; Hu, B. J. Org.
Chem. 1992, 57, 4309. (d) de Meijere, A.; Schulz, T.-J.; Kostikov,
R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547.
(12) A representative review: Hudlicky, T.; Reed, J. W. Angew. Chem.
Int. Ed. 2010, 49, 4864.
A solution of (Z)-1e (65 mg, 0.33 mmol) and 2a (77 mg, 0.30
mmol) in CH2Cl2 (3.0 mL) was added to (MeCN)4CuPF6 (2 mg,
0.005 mmol) in a flask at r.t. and stirred for 2 h under an argon
atmosphere. Extractive workup and purification of the residue
by chromatography on silica gel (CH2Cl2–MeOH = 200:1 to 40:1
as the eluent) afforded a mixture of (E)-3ea and 4ea [103 mg,
(E)-3ea/4ea = 5:95; (E)-3ea, 4% yield; 4ea, 77% yield] as a white
solid.
Analytical Data of 4ea
IR (KBr): 2982, 2935, 2873, 1728, 1711, 1693, 1490, 1479, 1447,
1369, 1317, 1294, 1250, 1209, 1188, 1156, 1128, 1077, 1066,
1011, 974, 920, 900, 827, 772, 762, 732 cm–1 1H NMR (400
.
MHz, CDCl3): δ = 7.43 (2 H, ddd, J = 8.4, 2.2, 2.2 Hz, ArH), 7.15 (2
H, ddd, J = 8.4, 2.2, 2.2 Hz, ArH), 5.50–5.40 (1 H, m, CH=CH2),
5.31–5.18 (2 H, m, CH=CH2), 4.95 (1 H, d, J = 7.2 Hz, 2-H), 3.90 [1
H, br, CH(CH3)2], 3.61 (3 H, s, OCH3), 3.59–3.47 [1 H, m,
CH(CH3)2], 2.89–2.77 (1 H, m, 3-H), 1.40–1.10 [6 H, m,
CH(CH3)2], 0.89 [3 H, d, J = 6.4 Hz, CH(CH3)2], 0.82 [3 H, d, J = 6.4
Hz, CH(CH3)2]. 13C NMR (100 MHz, CDCl3): δ = 171.9, 154.1,
134.2, 131.11, 131.08, 130.7, 121.7, 119.0, 60.6, 60.5, 52.7, 46.4,
46.0, 36.6, 33.9, 20.7, 20.6, 20.5, 20.3. ESI-HRMS: m/z [M + H]+
calcd for C20H27BrNO4: 424.1118; found: 424.1111.
(16) A study on decomposition of α-aryl diazoesters with rho-
dium(II) catalysts: Qu, Z.; Shi, W.; Wang, J. J. Org. Chem. 2001,
66, 8139.
(13) A study on cyclopropanation of (E)- and (Z)-enamides: Lu, T.;
Song, Z.; Hsung, R. P. Org. Lett. 2008, 10, 541.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 1880–1884