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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, P
A 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

Chirality

Volume

17

Pagination

44-50

ISSN

0899-0042

Department/School

School of Natural Sciences

Publisher

Wiley-Liss

Place of publication

Div John Wiley & Sons Inc, 605 Third Ave, New York

Rights statement

The definitive published version is available online at: http://interscience.wiley.com

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences