Synlett 2019; 30(11): 1339-1345
DOI: 10.1055/s-0037-1611828
letter
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of (Z)-Allyl Alcohols through Coinage-Metal-Catalyzed Nucleophilic Addition of Benzo[d]isoxazoles with Unactivated Propargyl Alcohols

a   Jiangxi Key Laboratory of Organic Chemistry Jiangxi Science and Technology Normal University, 605 Fenglin Road, Nanchang, Jiangxi 330013, P. R. of China   Email: pushouzhi@tsinghua.org.cn
b   Key Laboratory of Functional Small Organic Molecules, Ministry of Education, and College of Chemistry & Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China
,
Wenjin Wu
b   Key Laboratory of Functional Small Organic Molecules, Ministry of Education, and College of Chemistry & Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China
,
Tiantian Zheng
b   Key Laboratory of Functional Small Organic Molecules, Ministry of Education, and College of Chemistry & Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China
,
Jie Tan
b   Key Laboratory of Functional Small Organic Molecules, Ministry of Education, and College of Chemistry & Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China
,
Shouzhi Pu*
a   Jiangxi Key Laboratory of Organic Chemistry Jiangxi Science and Technology Normal University, 605 Fenglin Road, Nanchang, Jiangxi 330013, P. R. of China   Email: pushouzhi@tsinghua.org.cn
› Author Affiliations
We thank the China Postdoctoral Science Foundation (2017M612155), the Jiangxi Provincial Postdoctoral Foundation (2016RC37, and 2017KY44), and Natural Science Foundation of Jiangxi Province (20171BCB23038) for financial support.
Further Information

Publication History

Received: 31 March 2019

Accepted after revision: 28 April 2019

Publication Date:
13 May 2019 (online)


Abstract

The Au/Ag-cocatalyzed stereoselective addition reaction of cyanophenol anion species generated in situ with unactivated propargyl alcohols to produce functionalized (Z)-allyl alcohols in mostly good yields is reported. Benzo[d]isoxazoles were found to be excellent building blocks for the production of highly reactive cyanophenol anions from Kemp elimination reactions, thus serving as a masked benzonitrile source for the preparation of organonitrile derivatives. Silver salt combined with gold catalyst were found to be necessary for the success of this transformation.

Supporting Information

 
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  • 23 Representative Procedure for the Preparation of 3a: To a stirred solution of propargyl alcohol 1a (0.5 mmol) in anhydrous toluene (3.0 mL) was added Ph3PAuCl (0.025 mmol), AgOAc (0.05 mmol) and Li2CO3 (0.5 mmol) at room temperature. The reaction was purged with N2, and then benzo[d]isoxazole 2a (0.75 mmol) dissolved in toluene (1.0 mL) was added by using a syringe. The reaction was heated to 80 °C for ca. 4–6 h. After completion of the reaction as indicated by TLC, the reaction was allowed to cool to room temperature, diluted with ethyl acetate (5.0 mL), and extracted. The combined organic phase was washed with brine, dried over Na2SO4, and concentrated to give the crude residue, which was purified by silica column chromatography (elute: PE/EtOAc = 20:1 v/v) to give the desired product 3a. Yield: 135 mg (79%); yellow solid; mp 105–106 °C. 1H NMR (400 MHz, CDCl3): δ = 7.54–7.51 (m, 1 H), 7.41–7.36 (m, 2 H), 7.24–7.16 (m, 6 H), 7.04 (d, J = 7.6 Hz, 2 H), 6.92 (t, J = 7.6 Hz, 1 H), 6.69 (d, J = 8.8 Hz, 1 H), 6.04 (d, J = 8.8 Hz, 1 H), 5.60 (d, J = 8.4 Hz, 1 H), 2.24 (br, 1 H), 2.23 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 158.8, 148.8, 139.8, 137.6, 134.3, 133.9, 133.5, 133.4, 129.3, 128.8, 125.9, 122.3, 121.1, 116.1, 115.5, 102.2, 68.9, 21.1. HRMS: m/z [M + H]+ calcd for C23H20NO2: 342.1489; found: 342.1487.
  • 24 Representative Procedure for the Preparation of 4: A mixture of 3a (0.30 mmol), K2CO3 (0.45 mmol), and H2O2 (0.60 mmol) in DMSO (1.5 mL) was stirred at room temperature overnight. TLC was used to monitor the reaction until completion. Water (10 mL) was added, and the resulting mixture was extracted with ethyl acetate (3 × 10 mL). The combined organic solution was washed with brine, dried over MgSO4, and concentrated. The crude product was purified by silica gel column chromatography (PE/EtOAc = 2:1 v/v) to give the product 4. Yield: 72 mg (67%); colorless oil. 1H NMR (400 MHz, CDCl3): δ = 8.15–8.12 (m, 1 H), 7.66 (s, 1 H), 7.35 (br, 2 H), 7.22–7.09 (m, 6 H), 7.07–7.00 (m, 2 H), 6.98–6.96 (m, 1 H), 6.71 (d, J = 8.2 Hz, 1 H), 6.15 (d, J = 8.4 Hz, 1 H), 6.08 (d, J = 7.0 Hz, 1 H), 5.52 (d, J = 8.4 Hz, 1 H), 2.29 (br, 1 H), 2.24 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 166.7, 155.2, 148.4, 140.0, 137.8, 136.4, 133.4, 132.7, 129.4, 129.2, 128.8, 128.7, 126.1, 125.6, 122.5, 121.0, 115.1, 69.1, 21.1. HRMS: m/z [M + H]+ calcd for C23H22NO3: 360.1594; found: 360.1587.