research article

About the stereoelectronics of the intramolecular addition of allylsilanes to aldehydes

Schlosser, M.  
•
Franzini, L.
•
Bauer, C.
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2001
Chemistry - A European Journal

(Z)-omega-Trimethylsilyl-(omega-2)-alken-1-ols are readily accessible by consecutive superbase metalation and silylation of (omega-1)-alken-1-ols. These versatile intermediates may be oxidized to give the corresponding (Z)-omega-trimethylsilyl-(omega-2)-alkenals which, in the presence of trifluoroacetic acid, can be converted into 2-vinylcycloalkanols such as 2-vinylcyclohexanol (2), isopulegol (4), and bis(2-vinylcyclobutyl) ether (8). The stereochemical outcome of these cyclization reactions suggests the interference of a novel electrodynamic effect. [on SciFinder (R)]

Type
research article
DOI
10.1002/1521-3765(20010504)7:9%3C1909::AID-CHEM1909%3E3.0.CO;2-H
Author(s)
Schlosser, M.  
Franzini, L.
Bauer, C.
Leroux, F.  
Date Issued

2001

Published in
Chemistry - A European Journal
Volume

7

Issue

9

Start page

1909

End page

1014

Note

Section de Chimie de l'Universite, Lausanne-Dorigny, Switzerland 0947-6539 FIELD Electronic Internat.Standard Doc. Number: Germany: Germany, Federal Republic of Journal; Article; (JOURNAL ARTICLE) English

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSCO  
Available on Infoscience
March 3, 2006
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/226975