Indium(III)-Catalyzed Addition of 1,3-Dicarbonyl Compounds to Alkenes

Yu Yuan; Zhuangzhi Shi

doi:10.1055/s-2007-992388

LETTER

Indium(III)-Catalyzed Addition of 1,3-Dicarbonyl Compounds to Alkenes

Yu Yuan*, Zhuangzhi Shi
College of Chemistry & Chemical Engineering, Yangzhou University, 225002 Yangzhou, P. R. of China
Fax: +86(514)7975244; e-Mail: yyuan@yzu.edu.cn;

Abstract

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Abstract

A new InCl₃-catalyzed addition reaction of 1,3-dicarbonyl compounds to various alkenes proceeded in good yields and can be carried out in air, which provided an easy and practical procedure for carbon-carbon bond formation.

Key words

addition - indium - catalysis - alkene

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References

References and Notes

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18

All the products have been fully characterized by ¹H NMR (600 MHz) and ¹³C NMR (150 MHz) and the analyses were in agreement with published data. Data that were not found in the literature are as follows: Product 3b: ¹H NMR [600 MHz, CDCl₃; diastereomeric mixture (50:50)]: δ = 8.03-8.05 (m, 4 H), 7.93-7.96 (m, 4 H), 7.36-7.56 (m, 6 H), 6.85-6.94 (m, 4 H), 4.95 (d, J = 3.6 Hz, 1 H), 4.93 (d, J = 3.0 Hz, 1 H), 3.85 (s, 3 H), 3.81 (s, 3 H), 2.67-2.73 (m, 2 H), 2.24 (s, 2 H), 1.94 (s, 2 H), 1.55-1.64 (m, 2 H), 1.40-1.47 (m, 6 H), 1.25-1.30 (m, 2 H), 1.17-1.20 (m, 4 H), 1.07-1.12 (m, 2 H). ¹³C NMR [150 MHz, CDCl₃; diastereomeric mixture (50:50)]: δ = 196.22, 196.63, 194.31, 193.68, 163.89, 163.72, 137.27, 137.18, 133.44, 133.25, 131.42, 131.28, 130.26, 130.12, 128.94, 128.81, 128.77, 128.72, 114.12, 113.95, 64.57, 64.49, 55.57, 55.52, 43.62, 43.59, 39.84, 39.52, 37.48, 37.00, 36.77, 36.76, 36.05, 36.03, 30.10, 28.60, 28.58. HRMS: m/z calcd for C₂₃H₂₄O₃: 348.1725; found: 348.1720. Product 3c: ¹H NMR [600 MHz, CDCl₃; diastereomeric mixture (50:50)]: δ = 7.93-8.04 (m, 4 H), 7.28-7.65 (m, 12 H), 7.04-7.12 (m, 2 H), 5.02 (d, J = 11.4 Hz, 2 H), 3.81 (s, 3 H), 3.73 (s, 3 H), 2.68-2.72 (m, 2 H), 2.24 (s, 2 H), 1.95 (s, 2 H), 1.61-1.65 (m, 2 H), 1.48 (m, 6 H), 1.29 (m, 2 H), 1.20-1.21 (m, 4 H), 1.09-1.11 (m, 2 H). ¹³C NMR [150 MHz, CDCl₃; diastereomeric mixture (50:50)]: δ = 195.92, 195.69, 195.27, 195.00, 160.08, 159.94, 138.61, 138.55, 137.33, 137.25, 133.55, 133.35, 129.89, 129.74, 128.97, 128.82, 121.52, 121.40, 120.42, 120.31, 112.95, 112.73, 64.33, 55.47, 55.39, 43.81, 43.79, 39.74, 39.65, 37.39, 37.28, 36.78, 36.13, 30.13, 28.61. HRMS: m/z calcd for C₂₃H₂₄O₃: 348.1725; found: 348.1720. Product 3d: ¹H NMR [600 MHz, CDCl₃; diastereomeric mixture (48:52)]: δ = 7.77-7.96 (m, 8 H), 7.29-7.48 (m, 6 H), 7.10-7.19 (m, 4 H), 4.91 (d, J = 10.8 Hz, 2 H), 2.64 (m, 2 H), 2.33 (s, 3 H), 2.18 (s, 3 H), 2.16 (s, 2 H), 1.87 (s, 2 H), 1.53-1.56 (m, 2 H), 1.40 (m, 6 H), 1.19-1.22 (m, 2 H), 1.11-1.14 (m, 4 H), 1.03 (m, 2 H). ¹³C NMR [150 MHz, CDCl₃; diastereomeric mixture (48:52)]: δ = 196.06, 195.49, 195.46, 194.88, 144.57, 144.32, 137.27, 137.18, 134.77, 134.65, 133.48, 133.28, 129.66, 129.49, 129.15, 129.01, 128.95, 128.89, 128.78, 128.74, 64.39, 64.33, 43.70, 43.65, 39.78, 39.55, 37.45, 37.12, 36.76, 36.07, 30.11, 30.10, 28.60, 28.58, 21.73, 21.67. Anal. Calcd for C₂₃H₂₄O₂: C, 83.10; H, 7.28. Found: C, 82.84; H, 7.42. Product 3e: ¹H NMR [600 MHz, CDCl₃; diastereomeric mixture (50:50)]: δ = 7.88-8.04 (m, 8 H), 7.35-7.60 (m, 10 H), 4.93 (d, J = 11.4 Hz, 2 H), 2.69-2.72 (m, 2 H), 2.25 (s, 2 H), 1.94 (s, 1 H), 1.91 (s, 1 H), 1.60-1.62 (m, 2 H), 1.47 (m, 6 H), 1.27-1.29 (m, 2 H), 1.21-1.98 (m, 2 H), 1.06-1.10 (m, 2 H). ¹³C NMR [150 MHz, CDCl₃; diastereomeric mixture (50:50)]: δ = 195.84, 195.22, 194.77, 194.20, 140.17, 139.94, 137.11, 136.99, 135.44, 135.35, 133.75, 133.54, 130.40, 130.24, 129.27, 129.11, 129.02, 128.97, 128.86, 128.82, 64.95, 64.93, 43.60, 39.72, 39.67, 37.29, 37.22, 36.76, 36.05, 36.04, 30.09, 28.55. Anal. Calcd for C₂₂H₂₁ClO₂: C, 74.89; H, 6.00. Found: C, 74.50; H, 6.06. Product 3g: ¹H NMR [600 MHz, CDCl₃; diastereomeric mixture (48:52)]: δ = 7.90-7.93 (m, 4 H), 7.26-7.29 (m, 4 H), 4.26 (d, J = 11.4 Hz, 1 H), 4.20 (d, J = 11.4 Hz, 1 H), 2.50-2.57 (m, 2 H), 2.42 (s, 3 H), 2.41 (s, 3 H), 2.27 (s, 1 H), 2.19 (s, 1 H), 2.13 (s, 3 H), 2.10 (s, 3 H), 1.94 (s, 1 H), 1.81 (s, 1 H), 1.09-1.52 (m, 15 H), 0.86-0.88 (m, 1 H). ¹³C NMR [150 MHz, CDCl₃; diastereomeric mixture (48:52)]: δ = 204.65, 204.43, 196.00, 196.54, 144.82, 144.79, 134.93, 134.87, 129.62, 129.57, 70.66, 70.11, 42.53, 42.43, 40.19, 39.03, 37.25, 36.88, 36.72, 35.79, 35.72, 35.33, 30.11, 30.08, 28.60, 28.58, 27.33, 27.12, 21.75. HRMS: m/z calcd for C₁₈H₂₂O₂: 270.1620; found: 270.1620. Product 3h: ¹H NMR (600 MHz, CDCl₃): δ = 5.30 (s, 1 H), 4.02 (d, J = 6.6 Hz, 1 H), 2.40-2.41 (m, 1 H), 2.30-2.36 (m, 5 H), 1.05-1.98 (m, 10 H). ¹³C NMR (150 MHz, CDCl₃): d = 199.91, 176.84, 103.79, 81.35, 40.98, 39.81, 36.76, 35.38, 35.34, 29.36, 28.21, 24.21, 21.31. HRMS: m/z calcd for C₁₃H₁₈O₂: 206.1307; found: 206.1307. Product 6: ¹H NMR (600 MHz, CDCl₃): δ = 7.90 (d, J = 7.8 Hz, 2 H), 7.22 (d, J = 7.8 Hz, 2 H), 4.83 (d, J = 6.6 Hz, 1 H), 2.44 (d, J = 4.8 Hz, 1 H), 2.40 (s, 3 H), 2.33 (br s, 1 H), 1.82 (ddd, J = 2.4, 7.2, 13.8 Hz, 1 H), 1.45-1.65 (m, 4 H), 1.15-1.23 (m, 3 H). ¹³C NMR (150 MHz, CDCl₃): δ = 166.36, 143.35, 129.56, 129.03, 128.21, 77.98, 41.63, 39.74, 35.50, 28.28, 24.37, 21.70. HRMS: m/z calcd for C₁₅H₁₈O₂: 230.1307; found: 230.1307.