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COMMUNICATION
Journal Name
R. O’Connor, J. L Wood and B. M. Stoltz, Isr. J. Chem., 2016, 56
,
2013, 52, 4004–4007; enol ether: (
4
2
31–444; (
561–2567; (
f
) B. L. Pagenkopf and N. Vemula, Eur. J. Org. Chem., 2017,
) E. M. Budynina, K. L. Ivanov, I. D. Sorokin and M. Y.
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Org. Chem., 2018, 83, 5438–5499; ( ) A. O. Chagarovskiy, V. S. Vasin,
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Makhova and I. V. Trushkov, Angew. Chem. Int. Ed., 2018, 57, 10338– 8 H. Nambu, M. Fukumoto, W. Hirota, N. Ono and T. Yakura,
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Shumsky, V. B. Rybakov, L. G. Voskressensky and I. V. Trushkov, 9 K. W. Ratts and A. N. Yao, J. Org. Chem., 1966, 31, 1185–1188.
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g
malononitrile: (
Ghorai, J. Org. Chem., 2018, 83, 2131–2144; naphthol: (
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l
) A. Saha, A. Bhattacharyya, R. Talukdar and M. K.
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h
m
) T.
2
a
n
b
c
o
1
d
e
,
2065–2076.
1
1
583; (
614–1623; (
f
) R. K. Varshnaya and P. Banerjee, J. Org. Chem., 2019, 84
,
11 G. B. Payne, J. Org. Chem., 1967, 32, 3351–3355.
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) A. A. Akaev, S.
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13 H. Nambu, N. Ono, W. Hirota, M. Fukumoto and T. Yakura, Chem.
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3
4
3
60, 2938–2944.
We have also reported a ring-opening cyclization of spirocyclopropanes
with primary amines. (
Yakura, Org. Lett., 2014, 16, 4012–4015; (
Fukumoto, T. Tamura and T. Yakura, Chem. Eur. J., 2017, 23, 16799–
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) H. Nambu, M. Fukumoto, W. Hirota and T. 15 The reaction of 1a in the absence of 9 in refluxing CH Cl for 24 h
2 2
5
a
b
) H. Nambu, W. Hirota, M.
afforded 10 in 5% yield and the starting material 1a was recovered in
94% yield.
1
6805.
16 Aggarwal and co-workers reported that a similar proton transfer
event could intervene in sulfonium ylide-mediated cyclopropanations
under certain conditions. S. L. Riches, C. Saha, N. F. Filgueira, E.
6
(
a
) E. J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 1962, 84
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,
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) R. Appel, N. Hartmann and H. Mayr, J. Am.
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,
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d
McGarrigle, E. L. Myers, O. Illa, M. A. Shaw, S. L. Riches and V. K. 17 Crudden and co-workers also reported the deprotonation and
Aggarwal, Chem. Rev., 2007, 107, 5841–5883; ( ) X.-L. Sun and Y. reprotonation on the carbon atom of an -hydroxy sulfonium ylide in
Tang, Acc. Chem. Res., 2008, 41, 937–948; ( ) J.-R. Chen, X.-Q. Hu, the Corey–Chaykoxsky epoxidation. D. R. Edwards, J. Du and C. M.
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Lu, T.-R. Li, Q. Wang and W.-J. Xiao, Chem. Soc. Rev., 2017, 46 18 Although concerted mechanism for this reaction was also
135–4149; For recent examples, see: ( ) Q.-Z. Li, X. Zhang, R. Zeng,
Q.-S. Dai, Y. Liu, X.-D. Shen, H.-J. Leng, K.-C. Yang and J.-L. Li,
Org. Lett., 2018, 20, 3700–3704; ( ) J. Shao, W. Chen, M. Zhao, K. Shu,
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Sci., 2018, , 7091–7095; ( ) R. Hommelsheim, K. J. Hock, C. 20 (
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, 12753–12762; ( ) H. Mei, G. Pan, X. Zhang, L. Lin, X. Liu and X.
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Wang, Z.-J. Gao and J.-W. Xie, Adv. Synth. Catal., 2019, 361, 526–
e
f
g
9
,
a
4
h
considered, we proposed such a stepwise mechanism because it was
difficult to explain the high 2,3-trans stereoselectivity using the
concerted mechanism.
i
j) R. Oost, J. D. 19 For a leading review, see: H. C. Shen, Tetrahedron, 2009, 65, 3931–
3952.
9
k
a
) D. Harel, D. Schepmann, H. Prinz, R. Brun, T. J. Schmidt and B.
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l
D. Marson, D. Schepmann, T. J. Schmidt, S. Pricl and B. Wünsch, Eur.
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c
8
3
m
d
n
e
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2
34; (
o
) N. Punna, K. Harada, J. Zhou and N. Shibata, Org. Lett., 2019,
) F. Zhou, Y. Cheng, X.-P. Liu, J.-R. Chen and W.-J.
) S. Chen, J. Zhang, M.
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1
, 1515–1520; (p
Xiao, Chem. Commun., 2019, 55, 3117–3120; (
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q
Med. Chem. Lett., 2017,
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) J. Zhang, X. Liu,
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Liu and J. Xiao, Org. Lett., 2018, 20, 6069–6073; ( ) N. Hayama, R.
8, 96–101; (f) Y. Yang, J. Wang, Q. Wang, H.
7
Several reports on ring-opening reactions of cyclopropanes with carbon
nucleophiles have been published. Indole: (
Walker and J. S. Johnson, Org. Lett., 2013, 15, 2558–2561; (
Nanteuil, J. Loup and J. Waser, Org. Lett., 2013, 15, 3738–3741; (
Das, C. G. Daniliuc and A. Studer, Angew. Chem. Int. Ed., 2018, 57
053–4057; ( ) F. Chang, L. Lin, Y. Xia, H. Zhang, S. Dong, X. Liu
and X. Feng, Adv. Synth. Catal., 2018, 360, 2608–2612; arene: ( ) E.
a
) S. M. Wales, M. M. 21 For recent examples of chromane syntheses, see: (
) F. de
) S.
a
b
,
c
b
,
c
4
d
Kuramoto T. Földes, K. Nishibayashi, Y. Kobayashi, I. Pápai and Y.
Takemoto, J. Am. Chem. Soc., 2018, 140, 12216–12225.
e
Richmond, V. D. Vuković and J. Moran, Org. Lett., 2018, 20, 574–577; 22 M. J. Mphahlele and T. B. Moekwa, Org. Biomol. Chem., 2005,
) E. Richmond, J. Yi, V. D. Vuković, F. Sajadi, C. N. Rowley and J. 2469–2475.
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M. Fistikci, R. M. Carris and J. S. Johnson, Org. Lett., 2014, 16, 1626–
3,
(
f
9
g
1
3
629; enamine: (
58, 2053–2058; silyl enol ether: (
h
) K. Verma and P. Banerjee, Adv. Synth. Catal., 2016,
) J.-P. Qu, Y. Liang, H. Xu, X.-L.
) H.
i
Sun, Z.-X. Yu and Y. Tang, Chem. Eur. J., 2012, 18, 2196–2201; (
j
Xu, J.-P. Qu, S. Liao, H. Xiong and Y. Tang, Angew. Chem. Int. Ed.
,
4
| Chem. Commun., 2018, 00, 1‐4
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