Synthesis of 1-hydrocarbon substituted cyclopropyl silyl ketones

Article abstract of DOI:10.1016/j.tetlet.2018.09.017

The synthesis of cyclopropyl silyl ketones possessing a hydrocarbon group at 1-position of three-membered ring was investigated. The reaction of sulfoxonium ylide with α,β-unsaturated acylsilanes derived from α,β-unsaturated aldehydes did not afford the desired acylsilane derivatives. Instead, the corresponding silyl enol ethers were yielded exclusively. On the other hand, the Corey-Chaykovsky cyclopropanation of α-substituted α,β-unsaturated aldehydes proceeded well to give 1-substituted cyclopropyl aldehydes. The silyl substitution of formyl proton in the obtained aldehydes via umpolung of carbonyl group afforded the target acylsilanes.

Full text of DOI:10.1016/j.tetlet.2018.09.017

Tetrahedron Letters xxx (2018) xxx–xxx
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Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet
Synthesis of 1-hydrocarbon substituted cyclopropyl silyl ketones
⇑
Mitsunori Honda , Sho Sasaki, Tsuyoshi Nishimoto, Hiromoto Koshiro, Ko-Ki Kunimoto, Masahito Segi
Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa 920-1192, Japan
a r t i c l e i n f o
a b s t r a c t
Article history:
The synthesis of cyclopropyl silyl ketones possessing a hydrocarbon group at 1-position of three-mem-
Received 28 June 2018
Revised 28 August 2018
Accepted 6 September 2018
Available online xxxx
bered ring was investigated. The reaction of sulfoxonium ylide with
from ,b-unsaturated aldehydes did not afford the desired acylsilane derivatives. Instead, the corre-
sponding silyl enol ethers were yielded exclusively. On the other hand, the Corey-Chaykovsky cyclo-
propanation of -substituted ,b-unsaturated aldehydes proceeded well to give 1-substituted
a,b-unsaturated acylsilanes derived
a
a
a
cyclopropyl aldehydes. The silyl substitution of formyl proton in the obtained aldehydes via umpolung
of carbonyl group afforded the target acylsilanes.
Keywords:
Cyclopropyl silyl ketone
Ó 2018 Elsevier Ltd. All rights reserved.
a,b-Unsaturated aldehyde
Sulfoxonium ylide
Cyclopropanation
Umpolung
Introduction
Acylsilanes will become useful synthetic intermediates due to
specific properties of sterically congested and electrically positive
silyl group and carbonyl group that is one of the most reactive
organic functional groups [1]. We have currently investigated the
newly synthetic methods for functionalized acylsilanes [2] and
their synthetic utilities [3]. Especially, cyclopropyl silyl ketones
have attracted attention as useful synthetic intermediates, because
three specific reaction sites, cyclopropyl group, silyl group, and car-
bonyl group are present in one molecule [4]. Therefore we have
become interested in exploring the chemistry of cyclopropyl silyl
ketones. For example, we have previously described a route to
cyclopropyl silyl ketones via three steps beginning with simple
alkenes [5], and then reported that the efficient synthesis of silyl-
substituted dihydrofurans [6], silyl enol ethers or b-ketosilanes
[7] and the stereoselective synthesis of Z-homoallyl derivatives
[8] using specific reaction sites of cyclopropyl silyl ketones
(Scheme 1). Our synthetic method is convenient and gives many
kinds of cyclopropyl silyl ketones having various hydrocarbon sub-
stituents on 2- and/or 3-positions of three-membered ring. How-
ever, this procedure is valuable to make cyclopropyl silyl ketones
possessing an electrophilic group such as halogen, phenylthio
group, phenylseleno group on 1-position, but cannot afford 1-
hydrocarbon substituted cyclopropyl silyl ketones that would be
useful building brocks in organic synthesis for multiply substituted
hydrocarbon compounds [5a]. Hitherto, only one example of
Scheme 1. Synthesis and reactions of cyclopropyl silyl ketones.
synthesis of cyclopropyl silyl ketones having a methyl group on
1-position of cyclopropane ring has been reported by Danhaizer
about 30 years ago [4a,4e,9]. In this letter, we wish to describe
the investigation into the silylation and cyclopropanation of
a,b-
unsaturated aldehydes as starting materials in two routes to
prepare 1-hydrocarbon substituted cyclopropyl silyl ketones in
which no one has ever synthesized (Scheme 2). Herein we would
also like to state about the reaction behavior of
acylsilanes in Corey-Chaykovsky reaction [10].
a,b-unsaturated
⇑
Corresponding author.
E-mail address: honda@se.kanazawa-u.ac.jp (M. Honda).
https://doi.org/10.1016/j.tetlet.2018.09.017
0040-4039/Ó 2018 Elsevier Ltd. All rights reserved.
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2
M. Honda et al. / Tetrahedron Letters xxx (2018) xxx–xxx
reacted with acylsilane to give nearly the same result (Entry 3). The
reaction using ylide generated from sulfoxonium iodide with
sodium hydride instead of n-butyllithium preferentially provided
4 with low yield (Entry 4). In other reactions using different acyl-
silanes, 3 and 4 were also yielded independent of the kind of sub-
stituents on silicon atom or alkene moiety (Entries 5–7). Then the
cyclopropanation of 2-methylethenyl silyl ketone, which should
afford the desired 1-methyl substituted cyclopropyl silyl ketone,
also proceeded to give the corresponding silyl enol ether exclu-
sively (Entry 8). The results mentioned above suggest the following
mechanism for the reaction (Scheme 3). Generally, Corey-Chay-
kovsky cyclopropanation proceeds via 1,4-addition of sulfoxonium
Scheme 2. Two synthetic routes to cyclopropyl silyl ketones from a,b-unsaturated
aldehydes.
ylide to
a
,b-unsaturated ketone 2 to afford cyclopropyl ketone
,b-
through an intermediate A. However, in the reaction using
a
unsaturated silyl ketone and sulfur ylide, 1,2-addition took prece-
dence due to the resonance stabilization of allyl anions C and D
derived via Brook rearrangement [12] of silyl group through the
1,2-adduct intermediate B. Resultingly, the elimination of dimethyl
sulfoxide from allyl anion C gave the silyl enol ether 3 [7]. In other
words, the presence of easy rearrangeable silyl group prevents the
Results and discussion
Initially the cyclopropanation of a,b-unsaturated acylsilanes by
Corey-Chaykovsky reaction to obtain cyclopropyl silyl ketones 1
was carried out (Route a in Scheme 2). The results were summa-
rized in Table 1. First of all, to optimize the conditions of Corey-
Corey-Chaykovsky cyclopropanation of
a,b-unsaturated carbonyl
Chaykovsky reaction using
tion of readily accessible b-substituted
2 with dimethylsulfoxonium methylide was explored (Entries 1–
4). The b-substituted ,b-unsaturated acylsilanes 2 were prepared
according to the literature methods [2c]. The 3-phenyl substituted
ethenyl silyl ketones reacted with sulfoxonium ylide [11] that was
generated by the reaction of trimethylsulfoxonium iodide with n-
butyllithium. However, in these reactions, the Corey-Chaykovsky
cyclopropanation did not proceed at all, and the corresponding
silyl enol ethers 3 and hydrolyzed ketones 4 were exclusively
afforded (Entry 1). The reaction under low temperature showed
lower yield (Entry 2). The ylide derived from sulfoxonium chloride
a
,b-unsaturated acylsilanes, the reac-
compounds. These results strongly suggest that the target com-
pounds, 1-hydrocarbon substituted cyclopropyl silyl ketones can-
not be synthesized via route a in Scheme 2.
As mentioned above, it became clear that the presence of silyl
group interfered with the 1,4-addition of the ylide to the acylsi-
lanes that would lead to the formation of desired cyclopropyl
ketones, then the order of silylation and cyclopropanation using
a,b-unsaturated acylsilanes
a
a,b-unsaturated aldehydes were reversed (Route b in Scheme 2).
According to the literature, ,b-unsaturated aldehydes having a
a
n-hexyl, benzyl, isopropyl, or phenyl group were prepared from
simple and accessible aldehydes, as starting materials for cyclo-
propanation [13,14]. Firstly Corey-Chaykovsky reaction of enone
Table 1
Reaction of
a
,b-unsaturated acylsilanes 2 with dimetylsulfoxonium methylide.
Entry
1
Substrate
Temp. (°C)
Total yield (%)a
83
Relative ratio 3/4
r.t.
98/2
2
3
4
5
À50
r.t.
r.t.
50b
83b,c
22d
98b
92/8
>99/1
8/92
r.t.
>99/1
6
7
8
r.t.
r.t.
r.t.
61b
75b
70
84/16
90/10
>99/1
Molar ratio; acylsilane (2)/ylide = 1:1.2.
Ylide was generated by reaction of trimethylsulfoxonium iodide with n-BuLi.
a
Isolated yield.
b
Determined by 1H NMR.
c
Ylide was prepared from sulfoxonium chloride with n-BuLi.
Ylide was prepared from sulfoxonium iodide with NaH.
d
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M. Honda et al. / Tetrahedron Letters xxx (2018) xxx–xxx
3
Scheme 3. Plausible reaction mechanism.
5 with dimethylsulfoxonium methylide was investigated to con-
vert the olefin moiety of 5 into three-membered ring. The results
were summarized in Table 2. The reaction of 2-methyleneoctanal
with sulfoxonium ylide generated by the treatment of trimethyl-
sulfoxonium iodide with sodium hydride proceeded to afford the
corresponding cyclopropyl aldehyde 6 in good yield with the for-
mation of epoxide as a by-product 7 (Entry 1). Meanwhile, the
reaction using sulfoxonium ylide prepared by treating sulfoxonium
iodide with n-butyllithium in THF did not proceed well. In these
reactions, the desired cyclopropyl aldehydes were obtained inde-
1–4). Furthermore, the reaction of perillaldehyde gave the corre-
sponding cyclopropyl aldehyde possessing substituents on C1 and
C2 of cyclopropane ring (Entry 5). The obtained cyclopropyl alde-
hyde was a single diastereomer that was yielded by nucleophilic
attack of ylide from the same side of propenyl group on cyclohex-
ene plane. Though, it is unclear at present why this reaction pro-
ceeded with high stereoselectivity. In the near future, other
common cyclopropanation methods will be tried to investigate
the scope and limitations of this procedure.
Since the direct conversion of aldehyde 6 to silyl ketone 1 is
impossible, the umpolung of carbonyl group of 6 was employed
by thioacetal formation [15]. The aldehydes 6 were converted to
thioacetals 8 in good yields by reaction with 1,3-propanedithiol
and iodine [16]. These results were shown in Table 3. The deproto-
pendent with the kind of substituents on the
a-carbon (Entries
Table 2
Reaction of
a,b-unsaturated aldehydes 5 with dimetylsulfoxonium methylide.
Table 3
Protection and carbonyl umpolung of cyclopropyl aldehydes 6.
Entry
1
Substrate
Temp. (°C)
Total yield (%)
73a
Relative ratio
6/7
50
93/7
Entry
1
Substrate
Time (h)
1
Yielda (%)
96
2
3
50
r.t.
54a
48b
>99/1
2
3
23
20
77
65
96/4
4
r.t.
r.t.
94b
45a
>99/1
>99/1
4
5
1
1
66
56
5c
Molar ratio; enoene (5)/ylide = 1:1.2.
a
Isolated yield.
b
Determined by 1H NMR.
Molar ratio; cyclopropyl aldehyde (6)/HS(CH2)3SH/I2 = 1:1.1:0.1.
c
a
0.5 eq. of ylide was used.
Isolated yield.
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4
M. Honda et al. / Tetrahedron Letters xxx (2018) xxx–xxx
Table 5
nation of resulting thioacetals 8 with n-butyllithium, followed by
electrophilic reaction with chlorosilanes to 2-lithiodithiane inter-
mediates afforded 2-silylated 1,3-dithiane derivatives 9 [17]. The
results were summarized in Table 4. The reactivity of silylation
was affected by the kind of substituents on cyclopropane ring
and silyl group. The reaction of dithiane possessing n-hexyl group
on three-membered ring with Me3SiCl as a silylation reagent
promptly proceeded to afford the corresponding 2-silyldithiane 9
quantitatively (Entry 1). However, the yields decreased with the
increasing bulkiness of the silyl groups (Entries 2–4). In particular,
the reaction with t-BuMe2SiCl needed 24 h to the end (Entry 4),
and the substitution of i-Pr3Si group did not proceed at all (Entry
5). The silylation using silyl chloride having phenyl groups on sili-
con atom afforded a similar result (Entries 6–8). In an analogous
way, the yields of the reaction using cyclopropyldithianes 8 pos-
sessing substituent other than n-alkyl group on three-membered
ring decreased with the increasing bulkiness of the substituent
groups (Entries 9–12). Especially, the reaction of 1-phenylcyclo-
propyldithiane or bicyclo[4,1,0]heptyldithiane needed excessive
amounts of reactants to obtain the desired products in good yields
(Entries 11 and 12).
Synthesis of cyclopropyl silyl ketones 1.
Entry
1
R
Si
Yielda (%)
78
Me3Si
2
3
4
5
6
7
Et3Si
90
n-OctMe2Si
t-BuMe2Si
PhMe2Si
Ph2MeSi
Me3Si
56
Complex mixture
77
65
71
8
Me3Si
Me3Si
Me3Si
56
9
46
10
Trace
Finally, deprotection of 2-cyclopropyl-2-silyl-1,3-dithianes 9
was investigated. The treatment of silyldithianes 9 with iodine
and calcium carbonate in the THF/water combined solvent gave
the corresponding cyclopropyl silyl ketones 1 (Table 5) [18]. These
reactions proceeded in moderate to good yields independent of the
substituents on cyclopropane ring and silyl groups, except for the
reaction of cyclopropyldithiane having bulky silyl group and bicy-
clo[4,1,0]heptyldithiane (Entries 4 and 10). These results suggest
that the attack of iodide to sulfur atom of dithiane possessing a
huge alkyl or silyl group will be difficult. Since the dedithioacetal-
ization of silyldithiane having a phenyl group on cyclopropane
ring proceeded in moderate yield (Entry 9), the newest
convenient and efficient method was attempted (Scheme 4). The
Molar ratio; silyldithiane (9)/I2/CaCO3 = 1:6:6.
a
Isolated yield.
Scheme 4. Synthesis of acylsilane from the reaction using 30% H2O2 catalyzed by
Fe(III)-Nal.
Table 4
reaction of silyldithiane with 30% hydrogen peroxide catalyzed
by Fe(acac)3–NaI afforded the corresponding acylsilane in good
yield [19]. Though Kirihara have been reported that the deprotec-
tion methods gave different acylsilanes from the corresponding
dithiane derivatives in high yields independent of the kind of sub-
stituents [19], the reaction of bicyclo[4,1,0]heptyldithiane afforded
complex mixture in our case.
Silylation of dithiane derivatives 8.
Entry
1
R
Si
Time (h)
1
Yielda (%)
>99
Conclusion
Me3Si
In conclusion, synthesis of 1-hydrocarbon substituted cyclo-
2
3
4
5
6
7
8
Et3Si
1
1
57
67
63
–
70
66
–
propyl silyl ketones starting from
been described. The Corey-Chaykovsky cyclopropanation reaction
of ,b-unsaturated acylsilanes derived from silylation of the corre-
a,b-unsaturated aldehydes has
n-OctMe2Si
t-BuMe2Si
i-Pr3Si
PhMe2Si
Ph2MeSi
Ph3Si
24
24
24
24
24
a
sponding aldehydes did not proceed to give the desired 1-alkyl
substituted cyclopropyl silyl ketones at all. In these reactions the
corresponding silyl enol ethers or hydrolyzed ketones were exclu-
sively afforded via Brook rearrangement. Therefore, the order of
9
10
Me3Si
Me3Si
1
1
53
67
silylation and cyclopropanation using
were reversed. The Corey-Chaykovsky cyclopropanation of
stituted ,b-unsaturated aldehydes with dimethylsulfoxonium
a,b-unsaturated aldehydes
a-sub-
11b
12c
Me3Si
Me3Si
1
1
82
92
a
methylide proceeded well to yield the cyclopropyl aldehydes.
Before silylation of carbonyl group in the obtained aldehydes,
umpolung of the carbonyl group via formation of dithiane deriva-
tives from aldehydes was carried out. The deprotonation of result-
ing thioacetals with n-butyllithium, followed by electrophilic
reaction with chlorosilanes to 2-lithiodithiane intermediates
afforded 2-silylated 1,3-dithiane derivatives. Finally, deprotection
of 2-cyclopropyl-2-silyl-1,3-dithianes with iodine or hydrogen
Molar ratio; dithiane (8)/n-BuLi/SiCl = 1:2.0:2.4.
a
Isolated yield.
8 eq. of n-BuLi and 10 eq. of Me3SiCl were used.
4 eq. of n-BuLi and 5 eq. of Me3SiCl were used.
b
c
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M. Honda et al. / Tetrahedron Letters xxx (2018) xxx–xxx
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desired acylsilanes. Further studies are aimed at expanding the
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