Chemical Science
Edge Article
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these as reactive conformations in tranannular carbonyl-
olen metathesis reactions and investigated them
computationally. Specically, our computational results
suggest that conformation 14 (B2 ) is the one leading to
product formation under our optimized reaction conditions
b
for transannular carbonyl-olen metathesis.
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P. Gandeepan, T. Muller, D. Zell, G. Cera, S. Warratz and
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M. Charaschanya and J. Aube, Nat. Commun., 2018, 9, 934,
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In comparison, conformation 14 (B1 ) was found to lead to the
DOI: 10.1038/s41467-018-03248-2.
preferential formation of diastereomeric product epi-16 that is
not observed experimentally under our optimal reaction
conditions. See ESI for details.†
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20 For
a
Brønsted acid-catalyzed oxetane fragmentation
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L. Lorenc, L. Bondarenko, M. Rajkovic, A. Milavanovic and
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14 Efforts undertaken by Khirpach and coworkers to protect
´
details: (a) See ref. 11a; (b) M. Lj. Mihailovic, Lj. Lorenc,
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J. Forsek, H. Nesovic, G. Snatzke and P. Trska, Tetrahedron,
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a
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A. Milovanovic and M. Lj. Mihailovic, J. Chem. Soc., Perkin
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treatment with 3 equivalents of BF3$Et2O was reported to
form a transannular carbonyl–olen metathesis product:
V. A. Khripach, V. N. Zhabinskii, A. I. Kuchto,
10274 | Chem. Sci., 2019, 10, 10267–10274
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