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An unexpected allyl-transfer reaction under conditions of Lewis acid-promoted cyclization of homoallylic alcohols with aldehydes

Vyacheslav Vladimirovich Samoshin 1
Vyacheslav Vladimirovich Samoshin
, 
Irina P Smoliakova 2
Irina P Smoliakova
, 
Mingming Han 2
Mingming Han
, 
Paul H Gross 1
Paul H Gross
10.1070/MC1999v009n06ABEH001180
Published 1999-11-25
Communication , Volume 9, Issue 6, 219-221
7
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Samoshin V. V. et al. An unexpected allyl-transfer reaction under conditions of Lewis acid-promoted cyclization of homoallylic alcohols with aldehydes // Mendeleev Communications. 1999. Vol. 9. No. 6. pp. 219-221.
GOST all authors (up to 50) Copy
Samoshin V. V., Smoliakova I. P., Han M., Gross P. H. An unexpected allyl-transfer reaction under conditions of Lewis acid-promoted cyclization of homoallylic alcohols with aldehydes // Mendeleev Communications. 1999. Vol. 9. No. 6. pp. 219-221.
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TY - JOUR
DO - 10.1070/MC1999v009n06ABEH001180
UR - https://mendcomm.colab.ws/publications/10.1070/MC1999v009n06ABEH001180
TI - An unexpected allyl-transfer reaction under conditions of Lewis acid-promoted cyclization of homoallylic alcohols with aldehydes
T2 - Mendeleev Communications
AU - Samoshin, Vyacheslav Vladimirovich
AU - Smoliakova, Irina P
AU - Han, Mingming
AU - Gross, Paul H
PY - 1999
DA - 1999/11/25
PB - Mendeleev Communications
SP - 219-221
IS - 6
VL - 9
ER -
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@article{1999_Samoshin,
author = {Vyacheslav Vladimirovich Samoshin and Irina P Smoliakova and Mingming Han and Paul H Gross},
title = {An unexpected allyl-transfer reaction under conditions of Lewis acid-promoted cyclization of homoallylic alcohols with aldehydes},
journal = {Mendeleev Communications},
year = {1999},
volume = {9},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1999v009n06ABEH001180},
number = {6},
pages = {219--221},
doi = {10.1070/MC1999v009n06ABEH001180}
}
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Samoshin, Vyacheslav Vladimirovich, et al. “An unexpected allyl-transfer reaction under conditions of Lewis acid-promoted cyclization of homoallylic alcohols with aldehydes.” Mendeleev Communications, vol. 9, no. 6, Nov. 1999, pp. 219-221. https://mendcomm.colab.ws/publications/10.1070/MC1999v009n06ABEH001180.

Abstract

The title reaction was observed along with cyclization in the SnCl4-promoted reaction of 2-[3,4,6-tri-O-benzyl-2-deoxy-2-(p-tolylsulfanyl)-β-D-glucopyranosyl]ethanal with pent-4-en-2-ol and this result was interpreted in terms of anchimeric assistance by sulfur to the unusual fragmentation of an intermediate alkoxycarbenium ion.

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