Pentafulvene-derived η3-allyltitanocenes as intermediates for the stereoselective functionalization of 5-membered carbocycles

Jomy Joseph; Florian Jaroschik; K. V. Radhakrishnan; Jean-Luc Vasse; Jan Szymoniak

doi:10.1039/C3CC41826J

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Pentafulvene-derived η³-allyltitanocenes as intermediates for the stereoselective functionalization of 5-membered carbocycles†

Jomy Joseph,^a Florian Jaroschik,^a K. V. Radhakrishnan,^b Jean-Luc Vasse*^a and Jan Szymoniak*^a

Author affiliations

* Corresponding authors

^a Institut de Chimie Moléculaire, CNRS (UMR 7312) and Université de Reims, 51687 Reims Cedex 2, France
E-mail: jan.szymoniak@univ-reims.fr, jean-luc.vasse@univ-reims.fr
Fax: +33 (0)326913244
Tel: +33 (0)326913166

^b National Institute for Interdisciplinary Science and Technology, CSIR-NIIST, Industrial Estate. P. O., Trivandrum-19, Kerala, India

Abstract

Allyltitanocene complexes can be generated by reacting pentafulvenes with DIBAL-H and Cp₂TiCl₂. Their coupling with aldehydes affords homoallylic alcohols in a highly regio- and stereoselective manner. The potential of this method for the stereoselective synthesis of cyclopentane derivatives is illustrated.

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Article information

DOI: https://doi.org/10.1039/C3CC41826J
Article type: Communication
Submitted: 11 Mar 2013
Accepted: 22 Mar 2013
First published: 25 Mar 2013

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Chem. Commun., 2013,49, 4549-4551

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Pentafulvene-derived η³-allyltitanocenes as intermediates for the stereoselective functionalization of 5-membered carbocycles

J. Joseph, F. Jaroschik, K. V. Radhakrishnan, J. Vasse and J. Szymoniak, Chem. Commun., 2013, 49, 4549 DOI: 10.1039/C3CC41826J

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