Copper-Catalyzed Regiospecific and 1,2-Regioselective Cyclopropanation of (1Z)-1-Amino- and (1Z)-1-Oxy-1,3-butadienyl Derivatives

Abstract

The copper-catalyzed regiospecific and 1,2-regioselective cyclopropanation of (1Z)-1-amino- and (1Z)-1-oxy-1,3-butadienyl derivatives, which could be prepared by Z-stereoselective 1,4-elimination with α-aryl diazoesters was successfully demonstrated. This successful regiospecific protocol enabled the preparation of the corresponding 1-amino- and 1-oxy-2-vinylcyclopropane derivatives as almost single stereoisomers.

Key words

cycloaddition - diastereoselectivity - diazo compounds - regioselectivity - stereoselective synthesis

• References and Notes


Reviews:
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Preparation of 1-amino-2-vinyl (alkenyl) cyclopropanes:
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Preparation of 1-oxy-2-vinyl (alkenyl) cyclopropanes:
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• 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%].
• 15 Representative Procedure 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=CH ₂), 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(CH ₃)₂], 0.89 [3 H, d, J = 6.4 Hz, CH(CH ₃)₂], 0.82 [3 H, d, J = 6.4 Hz, CH(CH ₃)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 rhodium(II) catalysts: Qu Z, Shi W, Wang J. J. Org. Chem. 2001; 66: 8139