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Title: Catalytic asymmetric crotylation of aldehydes: application in total synthesis of (- )-elisabethadione
Authors: O'Hora, Paul
Incerti-Pradillos, Celia A.
Kabeshov, Mikhail A.
Shipilovskikh, Sergei A.
Rubtsov, Aleksandr E.
Elsegood, Mark R.J.
Malkov, Andrei V.
Keywords: Allylation
Asymmetric catalysis
Rearrangement
Stereoselectivity
Total synthesis
Issue Date: 2015
Publisher: © Wiley-VCH Verlag GmbH &Co
Citation: O'HORA, P. ... et al, 2015. Catalytic asymmetric crotylation of aldehydes: application in total synthesis of (- )-elisabethadione. Chemistry - A European Journal, 21(12), pp.4551-4555.
Abstract: A new, highly efficient Lewis base catalyst for a practical enantio- and diastereoselective crotylation of unsaturated aldehydes with E- and Z-crotyltrichlorosilanes has been developed. The method was employed as a key step in a novel asymmetric synthesis of bioactive serrulatane diterpene (À)-elisabethadione. Other strategic reactions for setting up the stereogenic centers included anionic oxy-Cope rearrangement and cationic cyclization. The synthetic route relies on simple, high yielding reactions and avoids use of protecting groups or chiral auxiliaries.
Description: This is the peer reviewed version of the following article: O'HORA, P. ... et al, 2015. Catalytic asymmetric crotylation of aldehydes: application in total synthesis of (- )-elisabethadione. Chemistry - A European Journal, 21(12), pp.4551-4555, which has been published in final form at http://dx.doi.org/10.1002/chem.201500176. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Sponsor: We thank the Leverhulme Trust for the Research grant F00 261AD and LU for studentships to P.O.H. and C.A .I.P.
Version: Accepted for publication
DOI: 10.1002/chem.201500176
URI: https://dspace.lboro.ac.uk/2134/16845
Publisher Link: http://dx.doi.org/10.1002/chem.201500176
ISSN: 0947-6539
Appears in Collections:Published Articles (Chemistry)

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