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Synlett 2012; 23(9): 1389-1393
DOI: 10.1055/s-0031-1290978
DOI: 10.1055/s-0031-1290978
letter
Highly Substituted Pyrroles by a Gold(I)-Catalyzed Tandem Reaction of 1-(1-Alkynyl)cyclopropyl Oxime Ethers with Nucleophiles
Further Information
Publication History
Received: 13 February 2012
Accepted after revision: 20 March 2012
Publication Date:
14 May 2012 (online)
Abstract
A gold(I)-catalyzed tandem reaction of 1-(1-alkynyl) cyclopropyl oxime ethers with nucleophiles under mild conditions has been developed, which provides a facile access to highly substituted pyrroles in moderate to excellent yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
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- 21 General Procedure for the Gold(I)-Catalyzed Tandem Reaction of 1-(1-Alkynyl)cyclopropyl Oxime Ethers with Nucleophiles A solution of PCy3AuOTf (generated from 1:1 mol ratio of PCy3AuCl/AgOTf, 3 mL, 0.005 M in toluene, 5 mol%) was added to a dry Schlenk tube under Ar. Oxime ether 1a (0.20 mmol, 57.8 mg) and nucleophile 2a (0.4 mmol, 43.3 mg) were added to the mixture. The resulting mixture was stirred at r.t. unless otherwise specified until the reactions were complete, as determined by TLC analysis. The residue was purified by flash column chromatography on silica gel (hexanes–EtOAc = 30:1) to afford the pure product 3a (0.17 mmol, 68.8 mg) in 87% yield; oil. 1H NMR (400 MHz, CDCl3): δ = 7.60–7.48 (m, 2 H), 7.30–7.04 (m, 13 H), 5.96 (s, 1 H), 4.42–4.34 (m, 2 H), 4.20 (d, J = 12.4 Hz, 1 H), 3.51 (s, 3 H), 2.92–2.86 (m, 1 H), 2.66–2.60 (m, 1 H), 1.80 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 142.22, 138.69, 131.57, 128.44, 128.20, 128.13, 127.54, 127.40, 127.28, 126.88, 125.77, 125.68, 125.60, 124.06, 112.25, 104.78, 82.63, 70.43, 65.07, 35.59, 8.08 ppm. IR (neat): ν = 1602, 1517, 1493, 1452, 1351, 1263, 1238, 1218, 1068, 1026, 971, 910 cm–1. MS (EI): m/z (%): 397 (15.33) [M]+, 91 (100). HRMS: m/z calcd for C27H27NO2: 397.2042; found: 397.2045
For reviews on pyrrole synthesis, see:
For recent examples of the Hantzsch synthesis, see:
For recent examples of Paal–Knorr reaction, see:
For recent examples on the pyrrole synthesis based on the transition-metal-catalyzed process, see: