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E. J. Phipps et al.
Letter
Synlett
Supporting Information
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Supporting information for this article is available online at
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References and Notes
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(15) General Procedure
N-Enoxyphthalimide (0.1 mmol), catalyst [Cp*CF3RhCl2]2 (5
mol%, 0.005 mmol, 3.7 mg), and CsOAc (2 equiv, 0.2 mmol, 38.5
mg) were weighed in a 1-dram vial with a magnetic stir bar. TFE
(0.2 M, 500 L) was added followed by alkene (1.2 equiv, 0.12
mmol). The vial was sealed with a screw cap and stirred at room
temperature for 12 h. Upon completion judged by TLC, the
crude solution was diluted with EtOAc and partitioned with the
addition of DI water. The aqueous layer was extracted three
times with EtOAc, and the combined organic extracts were fil-
tered through a pad of Celite® and Na2SO4 then concentrated.
The crude residue was purified by flash chromatography (hex-
ane/EtOAc, 19:1) to afford the cyclopropane product.
Compound 3ad: Purified by flash chromatography eluting with
5% EtOAc in hexanes; 21.0 mg, 98% yield, colorless oil, Rf = 0.73
1
(4:1 hexanes/EtOAc). H NMR (500 MHz, CDCl3): = 8.06–7.97
(m, 2 H), 7.59–7.51 (m, 1 H), 7.51–7.43 (m, 2 H), 2.51 (dd, J = 7.3,
5.4 Hz, 1 H), 1.70–1.39 (m, 10 H), 1.19 (dt, J = 12.6, 6.1 Hz, 1 H),
0.95 (dd, J = 7.4, 4.0 Hz, 1 H). 13C NMR (126 MHz, CDCl3): =
198.4, 139.1, 132.5, 128.6, 128.2, 38.0, 35.6, 32.2, 28.48, 26.3,
26.2, 26.0, 21.5. IR (neat): 2921, 2850, 1664, 1447, 1396, 1216,
980, 718, 689 cm–1. LRMS (ESI APCI): m/z calcd for C15H18O [M +
H]: 215.1; found: 215.1.
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Chem. 1995, 60, 6214.
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Shukla, M. K.; Vijayasree, U. Org. Lett. 2010, 11, 5466. (d) Vanier,
© 2019. Thieme. All rights reserved. — Synlett 2019, 30, A–D