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Cover Picture: Stereochemical Divergence in the Formation of Organic Carbonates Derived from Internal Epoxides (Adv. Synth. Catal. 11‐12/2013)
Author(s) -
Whiteoak Christopher J.,
Martin Eddy,
EscuderoAdán Eduardo,
Kleij Arjan W.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201390024
Subject(s) - chemistry , stereoselectivity , reagent , bicyclic molecule , organic synthesis , stereochemistry , ring (chemistry) , epoxide , catalysis , organic chemistry
The front cover picture, provided by Christopher J. Whiteoak, Eddy Martin, Eduardo Escudero‐Adbn and Arjan W. Kleij, illustrates the stereodivergent behavior when diastereoisomerically pure internal epoxides are converted into their organic carbonates using CO 2 as reagent under iron(III) catalysis. The stereodivergent behavior relates to two mechanistically different ring‐closure pathways, one leading to formal retention of configuration (outer‐sphere pathway) and the other giving rise to formal inversion of configuration (inner‐sphere pathway). The key parameters that guide the overall stereoselectivity have been investigated and a series of other challenging internal epoxides were successfully converted into their respective cyclic carbonates in high yield and diastereoselectivity (> 99%). This methodology is illustrated in the Full Paper by Whiteoak, Martin, Escudero‐Adbn and Kleij on pages 2233–2239 (DOI: 10.1002/adsc.201201070) .