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Synlett 2007(20): 3219-3223  
DOI: 10.1055/s-2007-992388
LETTER
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 14 September 2007
Publication Date:
03 December 2007 (online)

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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

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.