Please use this identifier to cite or link to this item: https://doi.org/10.1002/ejic.200500549
Title: Asymmetric [2+2] cycloaddition of (E)-2-(diphenylphosphanyl)styrene promoted by a chiral metal template
Authors: Yeo, W.-C. 
Tan, G.-K.
Lip, L.K. 
Leung, P.-H.
Keywords: Asymmetric synthesis
Cycloaddition
Phosphane ligands
Platinum
Template synthesis
Issue Date: 2-Dec-2005
Citation: Yeo, W.-C., Tan, G.-K., Lip, L.K., Leung, P.-H. (2005-12-02). Asymmetric [2+2] cycloaddition of (E)-2-(diphenylphosphanyl)styrene promoted by a chiral metal template. European Journal of Inorganic Chemistry (23) : 4723-4728. ScholarBank@NUS Repository. https://doi.org/10.1002/ejic.200500549
Abstract: An organoplatinum complex containing the (S)-form of orthometalated [1-(dimethylamino)ethyl]naphthalene as the chiral auxiliary promotes the asymmetric [2+2] dimerization of (E)-2-(diphenylphosphanyl)styrene to generate two isomeric chelating diphosphanyl-substituted cyclobutane platinum template complexes in the ratio of 6:1. The four substituents on the cyclobutane rings adopt the pseudo-equatorial positions with an all-trans arrangement. The naphthylamine auxiliary can be removed chemoselectively from the template products by treatment with concentrated hydrochloric acid to form the corresponding dichloroplatinum(II) complexes, which, upon subsequent ligand displacement with aqueous cyanide, liberate the enantiomerically enriched free diphosphane ligand in high yields. Recomplexation of the liberated diphosphane to the (R)-form of the platinum template, followed by fractional crystallization, allows separation of the optically pure platinum template complex containing the diphosphane ligand (1R,2R,3R,4R)-1,2- bis(diphenylphosphanyl)-3,4-diphenylcyclobutane, from which the free diphosphane can be subsequently liberated efficiently. © Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Source Title: European Journal of Inorganic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/75611
ISSN: 14341948
DOI: 10.1002/ejic.200500549
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