High Atom Efficiency in Sc(OTf)3-Catalyzed Allylation of Aldehydes with Tetraallyltin

Article abstract of DOI:10.1002/adsc.200202207

The high atom efficiency was achieved through addition of Ac₂O in the Sc(OTf)₃-catalyzed allylation of aldehyde with tetraallytin in a 4:1 molar ratio.

Full text of DOI:10.1002/adsc.200202207

UPDATES
High Atom Efficiency in ScꢀOTf)3-Catalyzed Allylation of
Aldehydes with Tetraallyltin
Yoshifumi Nagano, Akihiro Orita, Junzo Otera*
Department of Applied Chemistry, Okayama University of Science, Ridai-cho, Okayama 700 ± 0005, Japan
Fax: * ‡ 81)-86-256-4292, e-mail: otera@high.ous.ac.jp
Received: December 25, 2002; Accepted: February 27, 2003
OH
Abstract: The high atom efficiency was achieved
Sn
4
R
R
through addition of Ac2O in the Sc*OTf)3-catalyzed
allylation of aldehyde with tetraallytin in a 4:1 molar
ratio.
2
+
Sc(OTf)3
CH3CN
O
1
+
2
R
H
OAc
Ac2O
Keywords: acylation; allylation; Lewis acids; scan-
dium; stannanes
3
ratio in CH3CN at 08C was investigated *Table 1). With
ªAtom efficiencyº is a central keyword in green a 5 mol % catalyst concentration relative to the alde-
chemistry.[1] Of great importance for access to this end hyde that is the most common level in various Sc*OTf)3-
is realization of a 100% yield by use of reactants just in catalyzed reactions, the yield was 80% *entry 1), a figure
the theoretical stoichiometry. The employment of the comparable with that obtained in aqueous media.[6]
least possible amount of catalyst as well as minimization Upon gradual reduction of the catalyst concentration,
of undesired side-products is also indispensable. In this it turned out that the yield was not significantly
sense, the reaction of carbonyls with tetraallyltin *1), decreased until the 0.1 mol % level where an 82% yield
that is a useful method to provide homoallylicalcohols,
was obtained *entry 2). This may be a rather surprising
is attractive because all four allyl residues of 1 can be outcome with such a low level of catalyst concentration;
utilized. This is much more advantageous than more nevertheless the attained figure is unsatisfactory from
popular protocols using allyltrialkylsilyl or alkyltrial- the standpoint of atom efficiency. Since we had become
kylstannyl reagents which transfer only one allyl moiety aware of the potential efficacy of Ac2O to accelerate the
out of four organicgroups on the silicon or tin. The
reaction rate in a similar system,[10] we decided to
reaction between 1 and an aldehyde in a 1:4 molar ratio scrutinize the effect of this additive in more detail. As we
was reported to be promoted by HCl[2] or methanol,[3] expected, the yield was improved by adding Ac2O and
yet the yields of desired homoallyl alcohols were not an almost perfect allylation was achieved when the
constantly high: more than 90% in some cases but less in additive was used in an equimolar amount to aldehyde
others. Ionicliquids were employed as reaction media in
*entry 3). Although the products were composed of
which theyieldswere70 ±93%.[4] Phenol wasfoundtobe homoallyl alcohol 2a and acetate 3a, the single product
an effective promoter for reaction with ketone affording 2a was obtained simply by subjecting the reaction
87 ±99% yields.[5] Lewis acids are potentially useful as mixture to alkaline hydrolysis while addition of Ac2O/
well, yet only brief mention was made of Sc*OTf)3[6] and pyridine to the reaction mixture furnished 3a in 97%
Cu*OTf)2[7] catalysts for reaction between 1 and PhCHO yield *Scheme 1). It should be noted that such an
to furnish 84 and 90% yields, respectively.[8] As part of improvement of yield was not induced by other anhy-
our project to explore highly atom-efficient processes drides under the same conditions but rather a decrease
catalyzed by Lewis acid,[9] we have disclosed that the in the yield compared to the blank experiment was
yield of Sc*OTf)3-catalyzed allylation of aldehydes with observed: 82% *blank); 67% with hexanoicanhydride;
1 is intensively improved simply by addition of acetic 42% with benzoicanhydride; 65% with methanesulfon-
anhydride *Ac2O) *Equation 1).
icanhydride; 76% with toluenesulfonicanhydride.
Obviously, the primary purpose of this study is the Needless to say, Ac2O itself cannot work as a promoter.
attainment of high yield through employment of 1 and When a mixture of 1 and PhCHO was exposed to Ac2O
aldehyde in a strict 1:4 ratio. Moreover, reduction of the in the absence of Sc*OTf)3, no reaction took place.
catalyst concentration to a minimum level is equally
Then, other Lewis acids were screened in the same
important for the high atom efficiency. Along this line, reaction *Table 2). The similar increase in the yield was
the reaction between 1 and PhCHO with a 1:4 molar attained with benzaldehyde *entries 1 ± 4) but virtually
Adv. Synth. Catal. 2003, 345, 643 ± 646
DOI: 10.1002/adsc.200202207
ꢀ 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
643

Yoshifumi Nagano et al.
UPDATES
Table 1. Screening of the amount of Sc*OTf)3 and the effect
*2) In general, the yield is higher than 90%.
of Ac2O.[a]
*3) Since the reaction is clean and virtually free from
contaminants, isolation of the desired product is
simple.
Entry
Sc*OTf)3
Ac2O
Yield [%]
2a
3a
2a ‡ 3a
The analogous increase of yield by adding Ac2O was
reported for the Sc*OTf)3-catalyzed allylation of elec-
tron-rich aldehydes with allyltrimethylsilane.[11] In this
case, the coexisting Ac2O serves for suppressing the
secondary reactions *like double allylation or ether
formation) of the resulting homoallyl alcohols through
in situ acetylation to furnish homoallyl acetates. Appa-
rently, our reaction is totally different because the
homoallyl alcohols remained in the final reaction
mixture. Recently, the utility of the combination of
Lewis acids with Brùnsted[12] or carboxylic[13] acids as
well as phenol[5] was well recognized. Thus, we checked
the possibility of activation by acetic acid that was in situ
produced as the reaction had proceeded. However,
addition of this acid in our protocol led to no increase in
the yield but the ether derived from the resulting
homoallyl alcohol was formed to some extent.
1[b]
2[c]
3[c]
5 mol %
0.1 mol %
0.1 mol %
±
±
80
82
39
±
±
59
80
82
98
1 equiv.
[a]
Reaction conditions: aldehyde *3 mmol), 1 *0.75 mmol),
Sc*OTf)3 *0.15 mmol, 5 mol % or 0.003 mmol, 0.1 mol %),
08C; yields determined by GLC.
Reaction time: 30 min.
Reaction time: 1 h.
[b]
[c]
K2CO3 (10 equiv.),
MeOH-H2O 9:1,
rt, 5 h
2a, 100% (GLC)
Sc(OTf)3
98 % (isolated)
(0.1 mol %)
1 (0.25 equiv.)
PhCHO +
Ac2O (15 equiv.),
pyridine, rt, 5 h.
Ac2O (1 equiv.)
CH3CN
C, 1 h
0
3a, 97% (GLC)
97 % (isolated)
Scheme 1.
When the reaction was conducted in the presence of a
catalytic amount *0.1 mol %) of triflic acid or triflic
no improvement was observed for nonanal with these anhydride but in the absence of metal triflate, the yields
Lewis acids *entries 5 ± 8) in contrast to a high yield with of the nonanal adduct were 75% and 79%, respectively,
Sc*OTf)3 *entry 9). Evidently, this catalyst is superior to nearly comparable to that in the Sc*OTf)3-catalyzed
the other Lewis acids in terms of generality.
reaction. However, when one equivalent of Ac2O was
Armed with these results, a variety of aldehydes was added in the presence of triflic acid or triflic anhydride,
subjected to the allylation as shown in Table 3, from which the yield was not increased so much, only up to 88% and
the effectiveness of Ac2O to increase the yield is apparent. 83%, respectively. In the Sc*OTf)3-catalyzed reaction,
The following comments are further worthy of note.
the addition of one equivalent of Ac2O resulted in an
increase in the yield of the nonanal adduct to 96% yield
*see Table 2, entry 9). Apparently, the triflicaicd or
anhydride that may possibly arise in situ from the metal
triflate plays no pivotal role in the present protocol.
*1) The reaction proceeded smoothly with a,b-unsatu-
rated, sterically bulky, and both aliphatic and
aromaticaldehydes. Even acid-sensitive substrates
are employable.
Table 2. Comparison of various Lewis acids.[a]
Entry
R
Lewis acid
Yield [%]
Total yield *2 ‡ 3)[b]
2[c]
1
2
Ph
Ph
Ph
Ph
C8H17
C8H17
C8H17
C8H17
C8H17
Bi*OTf)3
Cu*OTf)2
TMSOTf
BF3OEt2
Bi*OTf)3
Cu*OTf)2
TMSOTf
BF3OEt2
Sc*OTf)3
97 *2a, 33; 3a, 64)
99 *2a, 29; 3a, 70)
86 *2a, 35; 3a, 51)
93 *2a, 42; 3a, 51)
83 *2b, 43; 3b, 40)
89 *2b, 60; 3b, 29)
86 *2b, 60; 3b, 26)
75 *2b, 62; 3b, 13)
96[e] *2b, 37; 3b, 59)
2a, 80
2a, 75
2a, 51
2a, 61
2b, 81
2b, 81
2b, 84
2b, 73
2b, 71
3[d]
4
5
6
7
8
9
[a]
Reaction conditions: aldehyde *3 mmol), 1 *0.75 mmol), Lewis acid *0.003 mmol), 08C, 1 h; yields determined by GLC.
With Ac2O *3 mmol).
Without Ac2O.
[b]
[c]
[d]
Reaction time: 2 h.
[e] A 94% yield of 2 was obtained after hydrolysis: Reaction conditions: 5.0 equiv. NaOMe in MeOH, rt, 5 h.
644
ꢀ 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
Adv. Synth. Catal. 2003, 345, 643 ± 646

Atom Efficiency in Sc*OTf)3-Catalyzed Allylation of Aldehydes
UPDATES
Table 3. Ac2O-preomoted Sc*OTf)3-catalyzed allylation of
Experimental Section
various aldehydes.[a]
General Methods
Entry
R
Yield [%]
All reactions were carried out under an atmosphere of argon
with freshly distilled solvents, unless otherwise noted. All
the solvents such as acetonitrile and pyridine were distilled
from CaH2. Metal triflates such as Sc*OTf)3, Cu*OTf)2 and
Me3SiOTf and BF3 ´ OEt2 were purchased and used without
purification. All the products were characterized by comparing
their spectral and physical data with the literature values: 2a,[15]
2b,[16] 2c,[15] 2e,[17] 2f,[18] 2 g,[19] 2 h,[15] 2i,[20] 3a,[21] 3b,[22] 3c,[21] 3g,[21]
3h,[21] and 3i.[23]
Total yield (2 + 3)[b]
2[c,d]
97 (2c, 62; 3c, 35)[f]
90 (2d, 42; 3d, 48)[h]
96 (2e, 33; 3e, 63)[f]
1[e]
2[g]
3[g]
2c, 96[f] (82)[f]
Ph
Ph
2d, 90[h] (65)[h]
2e, 96[f] (74)[f]
Ph
94 (2f, 25; 3f, 69)[h]
4[i]
2f, 95[h,j] (89)[h]
2g, 90[f,k] (64)[f]
90 (2g, 47; 3g, 43)[f]
95 (2h, 27; 3h, 68)[f]
94 (2i, 47; 3i, 47)[l]
5[e]
6[e]
7[e]
MeO
Representative Procedure for Allylation
2h, 98[f,k] (91)[f]
2i, 92[l] (71)[l]
To a mixture of PhCHO *318 mg, 3.0 mmol) and Sc*OTf)3
*1.5 mg, 0.003 mmol) in CH3CN *4 mL) was added tetraallyltin
*180 mL, 0.75 mmol) and Ac2O *0.28 mL, 3.0 mmol) in CH3CN
*1 mL) at 08C under Ar. The mixture was stirred for 1 h and
saturated aqueous NaHCO3 solution *10 mL) was added. After
usualwork-up*AcOEt/H2O), theorganiclayerwaswashedwith
brine. The organiclayer was dried *Na 2SO4) and filtered. The
filtrate was evaporated. GLC analysis of the crude mixture
showed the formation of 2a *39% yield) and 3a *59% yield).
O2N
O
2j, 92[h] (66)[h]
92 (2j, 68; 3j, 24)[l]
8[i]
THPO
8
[a] Reaction conditions: 3 mmol aldehyde, 0.25 equiv. 1, 0.1 mol %
Sc(OTf)3, 0 °C.
[b] With 1 equiv. Ac2O.
[c] After hydrolysis: Reaction conditions: 5.0 equiv. NaOMe in MeOH, rt,
5 h.
[d] Yield of 2 without Ac2O in parentheses.
[e] Reaction time: 1 h.
[f] Determined by GLC.
Representative Procedure for Homoallyl Alcohols in
One Pot
[g] Reaction time: 3 h.
[h] Isolated yields.
[i] Reaction time: 2 h.
[j] Reaction temp.: 40 °C, Reaction time: 12 h.
[k] Reaction conditions: 10 equiv. K2CO3 in MeOH/water (9:1), rt, 5 h.
[l] Determined by 1H NMR.
To a mixture of PhCHO *318 mg, 3.0 mmol) and Sc*OTf)3
*1.5 mg, 0.003 mmol) in CH3CN *4 mL) was added tetraallyltin
*180 mL, 0.75 mmol) and Ac2O *0.28 mL, 3.0 mmol) in CH3CN
*1 mL) at 08C under Ar, and the mixture was stirred for 1 h. To
the mixture were added K2CO3 *4.14 g, 30 mmol), MeOH
*4.5 mL) and H2O *0.5 mL) at 08C, and the mixture was stirred
at room temperature for 5 h. To this mixture, 1 N aqueous HCl
was added until the solution turned to pH 7. After usual work-
up *AcOEt/H2O), the organiclayer was washed with brine. The
organiclayer was dried *Na 2SO4) and filtered. The filtrate was
evaporated. GLC analysis of the crude mixture showed the
formation of 2a *100% yield). Subjection of the crude mixture
to column chromatography on silica gel *15% AcOEt/hexane)
provided 2a in a 98% yield *435 mg).
Upon addition of Ac2O *1 equiv.) to Sc*OTf)3 *1
equiv.) in CH3CN, the color of the solution turned faintly
yellow indicative of interaction between these two
components. While a 13C NMR spectrum of the solution
exhibited no change from free Ac2O, an IR spectrum
gave rise to low wavenumber shifts of carbonyl stretch-
ing bands in the presence of Sc*OTf)3.[14] As such, it is
deduced that an Sc*OTf)3 species that is weekly
coordinated by Ac2O is responsible for increasing the
allylation yield.
Representative Procedure for Homoallyl Acetates in
One Pot
In summary, we have arrived at a considerably high To a mixture of PhCHO *318 mg, 3.0 mmol) and Sc*OTf)3
*1.5 mg, 0.003 mmol) in CH3CN *4 mL) was added tetraallyltin
*180 mL, 0.75 mmol) and Ac2O *0.28 mL, 3.0 mmol) in CH3CN
*1 mL) at 08C under Ar, and the mixture was stirred for 1 h. To
the mixture were added pyridine *5 mL) and Ac2O *4.25 mL,
45 mmol) at 08C, and the mixture was stirred at room
temperature for 5 h. After addition of aqueous 1 N HCl
*10 mL) at 08C and usual work-up *AcOEt/H2O), the organic
layer was washed with aqueous NaHCO3 and brine. The
organiclayer was dried *Na 2SO4) and filtered. The filtrate was
evaporated. GLC analysis of the crude mixture showed the
formation of 3a *97% yield). Subjection of the crude mixture to
level of atom efficiency. All of the four allyl residues
together with an aldehyde component are consumed
and hence, no organotin species remains. Another
notable feature is the use of a tiny amount of the
catalyst. In the reaction using 3 mmol of aldehyde, the
necessary amount of Sc*OTf)3 is only 1.5 mg. This is
extremely economical and, in addition, advantageous in
separation of the catalyst residue from the product. As a
whole, the present protocol offers a highly atom-
efficient process for synthesis of homoallyl alcohols.
Adv. Synth. Catal. 2003, 345, 643 ± 646
asc.wiley-vch.de
ꢀ 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
645

Yoshifumi Nagano et al.
UPDATES
column chromatography on silica gel *5% AcOEt/hexane)
provided 3a in a 97% yield *551 mg).
McCluskey, I. W. Muderawan Muntari, D. J. Young, J.
Org. Chem. 2001, 66, 7811.
[4] C. M. Gordon, A. McCluskey, Chem. Commun. 1999,
1431.
[5] a) M. Yasuda, N. Kitahara, T. Fujibayashi, A. Baba,
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1-ꢀ6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)but-3-enol
ꢀ2d) *53:47 mixture of diastereomers): 1H NMR *CDCl3): d ˆ
ˆ
0.83, 0.85 *2 s, 3H), 1.15, 1.17 *2 d, J 8.6, 8.4 Hz, 1H), 1.30 *s,
3H), 1.55 *br, 1H), 2.07 ± 2.46 *m, 7H), 4.05 *dd, J 5.6, 6.9 Hz,
ˆ
1H), 5.09 ± 5.18 *m, 2H), 5.47 *br, 1H), 5.72 ± 5.89 *m, 1H);
13C NMR *CDCl3): d ˆ 21.3, 26.0, 26.1, 30.9, 31.5, 31.6, 37.6,
37.7, 39.3, 39.4, 40.8, 42.0, 73.47, 73.53, 117.36, 117.45, 117.54,
117.6, 134.8, 134.9, 149.3, 149.7; HRMS *EI): calcd. for
C13H20O: 192.1514; found: 192.1517.
[8] For other relevant papers on the use of tetraallyltin in
excess, see: a) D. N. Harpp, M. Gingras, J. Am. Chem.
Soc. 1988, 110, 7737; b) S. Fukuzawa, K. Sato, T. Fujina-
mi, S. Sakai, J. Chem. Soc. Chem. Commun. 1990, 939;
c) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61,
2256; d) N. Asao, S. Kii, H. Hanawa, K. Maruoaka,
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Greeves, E. G. McIver, Tetrahedron Lett. 1998, 39, 9238;
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Otera. Adv. Synth. Cat. 2002, 344, 84.
1-ꢀ8-Perhydro-2H-pyran-2-yloxyoctyl)but-3-enol
ꢀ2j):
1H NMR *CDCl3): d ˆ 1.31 ± 1.87 *m, 21H), 2.08 ± 2.18 *m,
ˆ
1H), 2.28 ± 2.35 *m, 1H), 3.38 *dt, J 6.7, 9.5 Hz, 1H), 3.47 ± 3.54
ˆ
*m, 1H), 3.60 ± 3.68 *m, 1H), 3.73 *dt, J 7.0, 9.5 Hz, 1H), 3.84 ±
ˆ
3.91 *m, 1H), 4.58 *dd, J 2.6, 4.4 Hz, 1H), 5.11 ± 5.17 *m, 2H),
5.76 ± 5.90 *m, 1H); 13C NMR *CDCl3): d ˆ 19.6, 25.4, 25.6,
26.1, 29.3, 29.46, 29.52, 29.7, 30.7, 36.7, 41.9, 62.3, 67.6, 70.6,
98.8, 118.0, 134.9; HRMS *EI): calcd. for C17H32O3: 284.2351;
found: 284.2341.
1-ꢀ6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)but-3-enyl
Acetate ꢀ3d) *52:48 mixture of diastereomers): 1H NMR
*CDCl3): d ˆ 0.78, 0.82 *2 s, 3H), 1.12, 1.13 *2 d, J ˆ 8.6 Hz, 1H),
1.29 *s, 3H), 2.01, 2.02 *2 s, 3H), 2.05 ± 2.12 *m, 1H), 2.18 ± 2.43
*m, 6H), 5.02 ± 5.10 *m, 2H), 5.17 ± 5.24 *m, 1H), 5.48 ± 5.52 *m,
1H), 5.62 ± 5.80 *m, 1H); 13C NMR *CDCl3): d ˆ 21.1, 21.2,
21.3, 26.1, 26.2, 31.0, 31.1, 31.4, 31.5, 36.7, 37.0, 37.8, 37.9, 40.7,
41.8, 42.4, 75.4, 75.6, 117.2, 117.3, 119.5, 121.0, 133.7, 133.9,
145.2, 145.9, 170.1, 170.2; HRMS *EI): calcd. for C15H22O2:
234.1620; found: 234.1633.
[10] A. Orita, Y. Nagano, K. Nakazawa, J. Otera, Synlett
2000, 599.
[11] V. K. Aggarwal, G. P. Vennall, Synthesis 1998, 1823.
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1-ꢀDiphenylmethyl)but-3-enyl Acetate ꢀ3e): 1H NMR
*CDCl3): d ˆ 1.81 *s, 3H), 2.15 ± 2.25 *m, 1H), 2.34 ± 2.42 *m,
1H), 4.10 *d, J ˆ 9.7 Hz, 1H), 4.95 ± 5.07 *m, 2H), 5.70 ± 5.84 *m,
2H), 7.14 ± 7.33 *m, 10H); 13C NMR *CDCl3): d ˆ 20.8, 37.5,
55.5, 74.1, 118.0, 126.5, 126.8, 128.2, 128.3, 128.4, 128.7, 133.4,
141.2, 141.3, 170.4; HRMS *EI): calcd. for C19H20O2: 280.1463;
found: 280.1469.
[13] a) M. V. Deaton, M. A. Ciufolini, Tetrahedron Lett. 1993,
34, 2409; b) M. A. Ciufolini, M. V. Deaton, S. Zhu, M.
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319.
1-ꢀ2,4,6-Trimethylphenyl)but-3-enyl Acetate ꢀ3f): 1H NMR
*CDCl3): d ˆ 2.04 *s, 3H), 2.24 *s, 3H), 2.42 *s, 6H), 2.51 ± 2.60
*m, 1H), 2.74 ± 2.84 *m, 1H), 5.02 ± 5.13 *m, 2H), 5.64 ± 5.78 *m,
1H), 6.18 *dd, J ˆ 6.4, 8.8 Hz, 1H), 6.81 *s, 2H); 13C NMR
*CDCl3): d ˆ 20.6, 20.8, 21.0, 38.2, 72.3, 117.6, 129.9, 132.9,
133.9, 136.3, 137.1, 170.2; HRMS *EI): calcd. for C15H20O2:
232.1463; found: 232.1478.
[14] n*C
bands in CH3CN: 1825 and 1755 cm±1 for free
ˆ
O)
Ac2O; 1806, 1754, 1671, 1625, 1597 cm±1 in the presence
of Sc*OTf)3.
[15] A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, Y. Tomonaga,
J. Org. Chem. 1990, 55, 2415.
1-ꢀ8-Perhydro-2H-pyran-2-yloxyoctyl)but-3-enyl Acetate
ꢀ3j): 1H NMR *CDCl3): d ˆ 1.28 ± 1.87 *m, 20H), 2.03 *s, 3H),
2.22 ± 2.37 *m, 2H), 3.38 *dt, J ˆ 6.7, 9.5 Hz, 1H), 3.46 ± 3.53 *m,
1H), 3.73 *dt, J ˆ 6.9, 9.5 Hz, 1H), 3.83 ± 3.91 *m, 1H), 4.57 *dd,
J ˆ 2.8, 4.2 Hz, 1H), 4.91 *quin, J ˆ 6.2 Hz, 1H), 5.04 ± 5.10 *m,
2H), 5.68 ± 5.82 *m, 1H); 13C NMR *CDCl3): d ˆ 19.6, 21.2,
25.2, 25.4, 26.1, 29.3, 29.4, 29.7, 30.7, 33.5, 38.6, 62.3, 67.6, 73.3,
98.8, 117.5, 133.7, 170.7; HRMS *EI): calcd. for C19H34O4:
326.2457; found: 326.2453.
[16] K. Yamada, T. Tozawa, M. Nishida, T. Mukaiyama, Bull.
Chem. Soc. Jpn. 1997, 70, 2301.
[17] T. Harada, T. Mukaiyama, Bull. Chem. Soc. Jpn. 1993,
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[18] H. Yamataka, K. Nishikawa, T. Hanafusa, Chem. Lett.
1990, 1711.
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Adv. Synth. Catal. 2003, 345, 643 ± 646