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Lewis acids screened included: Yb(OTf)3,
Sc(OTf)3, Zn(OTf)2, ZnBr2, MgCl2,
MgBr2, InBr3, TiCl4, Cu(OTf)2, and
BiCl3 at temperatures ranging from 0 ˚C
to refluxing and at ambient pressure to 1103 bar in a high-pressure
reactor.
<A NAME="RS07111ST-9">9</A>
Representative
Procedure for the Preparation of 4a
To a solution
of cyclobutane 1 (105 mg, 0.43 mmol, 1
equiv) and phenylacetylene (50 µL, 0.49 mmol, 1.1 equiv)
in DCE (6 mL, 0.1 M) was added BF3˙OEt2 (55 µL,
0.43 mmol, 1 equiv). A reflux condenser was quickly attached, and
the flask was placed in a preheated oil bath. After complete consumption
of the cyclobutane as indicated by TLC (15 min), the reaction mixture
was poured into a separatory funnel containing a half-saturated
solution of NaHCO3. The aqueous phase was extracted with
CH2Cl2 (3 × 5 mL),
and the combined organic extracts were washed with brine, dried over
MgSO4, filtered through a pad of Celite, and concentrated
in vacuo. The crude reaction product was purified by flash column
chromatography (hexanes-EtOAc = 4:1) to provide
the corresponding addition-rearrangement product 4a (79 mg, 53%) as a yellow oil. R
f
= 0.49
(hexanes-EtOAc = 4:1). ¹H
NMR (600 MHz, CDCl3): δ = 7.56-7.55 (m,
2 H), 7.31-7.29 (m, 2 H), 7.27-7.25 (m, 1 H),
5.72 (d, J = 8.8
Hz, 1 H), 5.53 (d, J = 8.8
Hz, 1 H), 4.32 (app t, J = 4.1
Hz, 2 H), 4.19 (q, J = 4.0
Hz, 4 H), 3.55 (t, J = 7.9 Hz,
1 H), 2.73 (d, J = 8.2
Hz, 2 H), 2.62 (app t, J = 4.1
Hz, 2 H), 1.25 (t, J = 7.0
Hz, 6 H). ¹³C NMR (100 MHz, CDCl3): δ = 169.0(2),
157.4, 137.5, 137.0, 128.3 (2), 128.1, 125.3 (2), 122.1, 99.1, 69.0,
61.5 (2), 51.0, 38.8, 37.1, 14.1 (2). HRMS: m/z calcd
for C20H24O5: 344.1624; found:
344.1617.
