+44 (0)1509 263171
Please use this identifier to cite or link to this item:
|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.
|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|
|Publisher Link: ||http://dx.doi.org/10.1002/chem.201500176|
|Appears in Collections:||Published Articles (Chemistry)|
Files associated with this item:
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.