TY - JOUR
T1 - Synthesis of spirocyclic heterocycles from α,β-unsaturated N -acyliminium ions
AU - Thaima, Thanphat
AU - Yazici, Arife
AU - Auranwiwat, Chiramet
AU - Willis, Anthony C.
AU - Wille, Uta
AU - Limtharakul, Thunwadee
AU - Pyne, Stephen G.
N1 - Publisher Copyright:
© 2021 The Royal Society of Chemistry.
PY - 2021/1/7
Y1 - 2021/1/7
N2 - The reactions of α,β-unsaturated N-acyliminium ions, generated in situ from 4(S)-O-substitutedhydroxy-5-hydroxy-5-vinyl-N-alkylpyrrolidin-2-ones, with allylsilanes and indoles leading to the formation of spirocyclic heterocycles, are reported. Six single crystal X-ray structures and extensive 2D NMR experiments confirmed the structures and stereochemistries of these products. In addition, computational studies provided mechanistic insights and an understanding of the stereochemical outcomes of these reactions.
AB - The reactions of α,β-unsaturated N-acyliminium ions, generated in situ from 4(S)-O-substitutedhydroxy-5-hydroxy-5-vinyl-N-alkylpyrrolidin-2-ones, with allylsilanes and indoles leading to the formation of spirocyclic heterocycles, are reported. Six single crystal X-ray structures and extensive 2D NMR experiments confirmed the structures and stereochemistries of these products. In addition, computational studies provided mechanistic insights and an understanding of the stereochemical outcomes of these reactions.
UR - http://www.scopus.com/inward/record.url?scp=85099134223&partnerID=8YFLogxK
U2 - 10.1039/d0ob02075c
DO - 10.1039/d0ob02075c
M3 - Article
SN - 1477-0520
VL - 19
SP - 259
EP - 272
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 1
ER -