V. V. Zhdankin et al. / Tetrahedron Letters 43 (2002) 2359–2361
2361
Acknowledgements
from dichloromethane/diethyl ether afforded 0.556 g (83%)
of product 4a in the form of a white, microcrystalline
solid; mp 108–110°C; IR (KBr): 3065, 1534, 1440, 1252,
1
512 cm−1; H NMR (CDCl3): l 7.27–7.66 (m, 20H, 4Ph),
This work was supported by a research grant from the
National Science Foundation (NSF/CHE-0101021) and
by a CRDF award RC2-2216. Special thanks are made
to Dr. Victor G. Young, Jr. and the X-ray Crystallo-
graphic Laboratory of the University of Minnesota for
X-ray structural analysis of compound 4a.
2.62 (s, 3H, CH3). 13C NMR (CDCl3): l 193.4 (CꢁO),
134–122 (4Ph), 121 (q, JCF=318 Hz, OTf), 118 (d, JCP
=
104 Hz, CꢁP), 27 (CH3). Anal. calcd for C28H23F3IO4PS:
C, 50.16; H, 3.46; I, 18.93; S, 4.78. Found: C, 49.72; H,
3.48; I, 19.01; S, 4.65%. FAB HRMS m/z 521.0504 (M−
OTf)+, calcd for C28H23F3IO4PS 521.05.
Preparation of 6a: A mixture of reagent 56 (0.196 mg, 0.5
mmol) and phosphonium ylide 2a (0.151 g, 0.5 mmol) in
dry dichloromethane was stirred overnight at room tem-
perature under nitrogen. The resulting solution was con-
centrated in vacuum yielding a slightly yellow oil. The oil
was recrystallized from dichloromethane and diethyl ester
to afford 0.170 g (50%) of product 6a as white crystals, mp
110–111°C; IR (KBr): 3050, 1550, 1223, 1176, 1114, 1031
References
1. (a) Varvoglis, A. The Organic Chemistry of Polycoordi-
nated Iodine; VCH Publishers: New York, 1992; (b) Var-
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V. V. Chem. Rev. 1996, 96, 1123–1178.
2. Pirkuliev, N. S.; Brel, V. K.; Zefirov, N. S. Russ. Chem.
1
cm−1; H NMR (CDCl3): l 7.4–8.0 (m, 20H), 7.34 (d, 2H,
Rev. 2000, 69, 105–120.
3. Moriarty, R. M.; Prakash, I.; Prakash, O.; Freeman, W.
A. J. Am. Chem. Soc. 1984, 106, 6082.
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5. Representative experimental data. Preparation of 4a: A
solution of ylide 2a (0.106 g, 0.335 mmol) in 3 ml
dichloromethane was added to a suspension of triflate 34
(0.221 g, 0.335 mmol) under a nitrogen atmosphere at
room temperature. The solution was additionally stirred
for 3 h, washed several times with water, dried, and
concentrated in vacuum. Recrystallization of the residue
J=8 Hz), 7.12 (d, 2H, J=8 Hz) 2.63 (s, 3H), 2.33 (s, 3H);
13C NMR (CDCl3): 190.0, 135–122 (4Ph and Ts), 119.0 (d,
J
CP=90 Hz), 22.9, 16.8. Anal. calcd for C34H30IO4PS: C,
58.97; H, 4.37; I, 18.32. Found C, 59.05; H, 4.34; I,
18.45%.
6. Koser, G. F. Aldrichim. Acta 2001, 34, 89.
7. Product 8a: Oil, 1H NMR (CDCl3): l 7.0–7.8 (m, 20H,
4Ph), 2.35 (s, 3H, CH3). 13C NMR (CDCl3): l 196.8
(CꢁO), 143–124 (4Ph), 55.5 (d, JCP=104.4 Hz, CꢁP), 25.5
(CH3). FAB HRMS m/z 427.13188 (M+H)+, calcd for
C27H24OPS 427.12855.