5
participation (NGP) in which intramolecular phenyl migration
D) and followed by cyclization gave the final product (3a).
References and notes
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1
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Ts
N
Ts
Ts
NH
AgOTf
N
-
AgOTf
AgOTf
Ph OH2
Ph
(e) Wolf, C.; Xu, H. Chem. Commun. 2011, 47, 3339.
1
a
Ph OH
2.
(a) Kang, B.; Miller, A. W.; Goyal, S.; Nguyen, S. B. T. Chem.
Commun. 2009, 3928; (b) Bergmann, E. D. Chem. Rev. 1953, 53,
H O
2
A
3
09; (c) Kumar, G. B.; Patel, H. V.; Shah, A. C.; Trenkle, M.;
Ts
NH
AgOTf
N Ts
Ts
Cardin, C. J. Tetrahedron Asymm.1996, 7, 3391; (d) Yadav, V. K.;
Sriramurthy, V. J. Am. Chem. Soc. 2005, 127, 16366; (e) Gandhi,
S.; Bisai, A.; Prasad, B. A. B.; Singh, V. K. J. Org. Chem. 2007,
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(a) Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132,
4
S.; Wen, Y.; Zhu, G. Tetrahedron Lett. 2010, 51, 5131; (c) Kang,
B.; Miller, A. W.; Goyal, S.; Nguyen, S. T. Chem. Commun. 2009,
3
(a) Fan, Y. C.; Kwon, O. Molecules 2011, 16, 3802; (b)
Sriramurthy, V.; Barcan, G. A.; Kwon, O. J. Am. Chem. Soc.
2
Elliott, L. D.; Wrigglesworth, J. W.; Cox, B.; Lloyd-Jones, G. C.;
Booker-Milburn, K. I. Org. Lett. 2011, 13, 728.
Shaghafi, M. B.; Grote, R. E.; Jarvo, E. R. Org. Lett. 2011, 13,
Ts
NH
Ts
NH
Ts
HN
N
AgOTf
Ph OH
-
AgOTf
Ph
O
H
O
A
1
a
B
3
4
.
.
570; (b) Chen, D.; Chen, X.; Du, T.; Kong, L.; Zhen, R.; Zhen,
Ts
N
Ts
Ts
H
NH
NH
NGP
Ph migration
+
AgOTf
AgOTf
+
928.
Ph
O
Ph
O
C
007, 129, 12928.
Ts
N
Ts
NH
5.
O
6
.
Ph
O
5
188.
7
8
.
.
Balaji, P. V.; Chandrasekaran, S. Chem. Commun. 2014, 50, 70.
Some of our important works: (a) Ghosal, N. C.; Santra, S.;
Kundu, K. S.; Hajra, A.; Zyryanov, G. V.; Majee, A. RSC Adv.
D
3a
2
015, 5, 56780; (b) Santra, S.; Kopchuk, D. S.; Kovalev, I. S.;
Scheme 4. Proposed reaction pathway.
Zyryanov, G. V.; Majee, A.; Charushin, V. N.; Chupakhin, O. N.
Green Chem. 2016, 18, 423; (c) Mitra, S.; Chakraborty, A.;
Mishra, S.; Majee, A. Hajra, A. Org. Lett. 2014, 16, 5652; (d)
Santra, S.; Mitra, S.; Bagdi, A. K.; Majee, A.; Hajra, A.
Tetrahedron Lett. 2014, 55, 5151; (e) Monir, K.; Ghosh, M.;
Mishra, S.; Majee, A. Hajra, A. Eur. J. Org. Chem. 2014, 1096;
(f) Monir, K.; Bagdi, A. K.; Ghosh, M.; Mishra, S.; Majee, A.
Hajra, Adv. Synth. Catal. 2014, 356, 1105; (g) Santra, S.; Bagdi,
A. K.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1065;
In conclusion, we have developed a one pot synthesis of 1,3-
oxazolidine derivatives by two different approaches. In the first
methodology we have used aziridines and styrenes. Whereas, in
the second approach we have developed an unprecedented
reaction of aziridines with in situ generated ring opening product
(B) of the aziridine itself. To the best of our knowledge there is
(h) Bagdi, A. K.; Rahman, M.; Santra, S.; Majee, A.; Hajra, A.
no such report in literature for this type of cyclization. We hope
this observation will be fruitful for academic, industrial and the
learned reader of Tetrahedron Letters.
Adv. Synth. Catal. 2013, 355, 1741.
9
.
(a) Ghosal, N. C.; Santra, S.; Das, S.; Hajra, A.; Zyryanov, G. V.;
Majee, A. Green Chem. 2016, 18, 565 and ref cited there in; (b)
For a Review see: Watson, D. G.; Yu, L; Yudin, A. K. Acc.
Chem. Res., 2006, 39, 194; (c) Sweeney, J. B. Chem. Soc. Rev.
Acknowledgments
2
002, 31, 247.
A. Majee and N. C. Ghosal are pleased to acknowledge the
financial support from BRNS-DAE, Govt. of India (Grant No.
Supplementary Material
3
7(2)/14/35/2014-BRNS/563). We are thankful to DST-FIST and
Supplementary data associated with this article can be found,
in the online version.
UGC-SAP. S. Santra and G. V. Zyryanov acknowledge the
Russian Science Foundation (Ref. # 16-43-02020) for funding.
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