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One-pot synthesis and chiral analysis of cyclopropane derivatives
journal contribution
posted on 2023-05-17, 00:13 authored by Ghanem, A, Aboul-Enein, HY, Muller, PA user-friendly, one-pot procedure was developed to access racemic as well as enantiomerically enriched cyclopropanes. Thus, the cyclopropanation of olefin (3) was performed using Meldrum's acid (4) or dimethyl malonate (5) and diacetoxyiodobenzene PhI(OAc)2 (6) or iodosyl benzene PhI=O (7) for in situ generation and decomposition of the phenyliodonium ylide 1 and 2, respectively. The reaction proceeds well with 5 mol% of achiral rhodium (II)-catalyst [Rh2(OAc)4] and a 10-fold excess of olefin affording the cyclopropane derivates 10 and 11, respectively, with high yield. The system is compatible with chiral Rh(II)-catalysts 8 and 9 and an enantiomeric excess up to 66% was achieved. An effective baseline separation of the enantiomers of the resulting cyclopropane derivatives was achieved using gas chromatography on the chiral stationary phase Chirasil--dex.
History
Publication title
ChiralityVolume
17Pagination
44-50ISSN
0899-0042Department/School
School of Natural SciencesPublisher
Wiley-LissPlace of publication
Div John Wiley & Sons Inc, 605 Third Ave, New YorkRights statement
The definitive published version is available online at: http://interscience.wiley.comRepository Status
- Restricted