Highly Substituted Pyrroles by a Gold(I)-Catalyzed Tandem Reaction of 
1-(1-Alkynyl)cyclopropyl Oxime Ethers with Nucleophiles

Yanqing Zhang; Junliang Zhang

doi:10.1055/s-0031-1290978

Synlett, Table of Contents

Synlett 2012; 23(9): 1389-1393
DOI: 10.1055/s-0031-1290978

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Highly Substituted Pyrroles by a Gold(I)-Catalyzed Tandem Reaction of 1-(1-Alkynyl)cyclopropyl Oxime Ethers with Nucleophiles

Yanqing Zhang

^aShanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North, Zhongshan Road, Shanghai 200062, P. R. of China

,

Junliang Zhang*

^aShanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North, Zhongshan Road, Shanghai 200062, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China, Fax: +86(21)62235039 Email: jlzhang@chem.ecnu.edu.cn

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Abstract

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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.

Key words

pyrroles - gold - nucleophiles - cyclization - cyclopropane

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References

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

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