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Synlett 2017; 28(20): 2829-2832
DOI: 10.1055/s-0036-1590742
DOI: 10.1055/s-0036-1590742
letter
Diastereoselective Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to α-Substituted Cyclic Enones
The authors acknowledge financial support from the National Natural Science Foundation of China (NSFC) (21532010, 21372242, 21472214, 21421091), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20030100), the NSFC and the Research Grants Council of Hong Kong Joint Research Scheme (21361162001), the Technology Commission of Shanghai Municipality, and the Croucher Foundation of Hong Kong.Further Information
Publication History
Received: 22 May 2017
Accepted after revision: 05 July 2017
Publication Date:
23 August 2017 (online)
This paper is dedicated to Professor Victor Snieckus on the occasion of his 80th birthday.
Abstract
A palladium-catalyzed conjugate addition of arylboronic acids to α-substituted cyclic enones was developed to give α,β-disubstituted ketones with high diastereoselectivity. Mechanistic investigation showed that the high diastereoselectivity was realized through epimerization.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590742.
- Supporting Information
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References and Notes
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- 11 Typical experimental procedure: To a flame-dried 25 mL Schlenk tube were added Pd(TFA)2 (4.2 mg, 0.0125 mmol), ligand L2 (2.3 mg, 0.015 mmol), and anhydrous DMAc (1.0 mL). The resulting mixture was stirred for 60 min. Arylboronic acid 2b (68.0 mg, 0.5 mmol) and ketone 1a (24.0 mg, 0.25 mmol) were added subsequently. The resulting reaction mixture was stirred at 80 °C for 24 h. Water (10 mL) was added and the aqueous phase was extracted with ethyl acetate (2 × 10 mL). The combined organic phase was washed with water (3 × 10 mL) and brine (10 mL). The organic phase was dried over anhydrous Na2SO4 and filtered. After the volatile materials were removed in vacuo, the ratio of two diastereoisomers was determined by GC chromatography. The resulting residue was then subjected to flash chromatography on silica gel with petroleum ether and ethyl acetate as eluent to give product 3b (39.9 mg, 85%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ = 7.33–7.01 (m, 5 H), 3.10 (td, J = 12.1, 5.2 Hz, 1 H), 2.61–2.48 (m, 1 H), 2.43–2.17 (m, 7 H), 1.87–1.71 (m, 1 H), 1.01 (dd, J = 6.8, 1.3 Hz, 3 H). 13C NMR (101 MHz, CDCl3): δ = 219.7, 140.3, 136.4, 130.6, 126.5, 126.4, 124.7, 51.0, 46.0, 37.6, 29.1, 19.8, 12.1. IR (neat): 2962, 1738, 1492, 1459, 1406, 1260, 1147, 1090, 1021, 798, 761, 732. MS (EI): m/z (%) = 187 (60) [M+], 132 (90), 114 (100), 90 (50). HRMS (EI): m/z [M]+ calcd for C13H16O: 188.1201; found: 188.1199.
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