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1987271 
Journal Article 
Solvent-Dependent Enantiodivergence in the Chlorocyclization of Unsaturated Carbamates 
Garzan, A; Jaganathan, A; Marzijarani, NS; Yousefi, R; Whitehead, DC; Jackson, JE; Borhan, B 
2013 
Yes 
Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765 
19 
27 
9015-9021 
English 
23671005 
WOS:000320782400034 
A remarkable solvent-controlled enantiodivergence is seen in the hydroquinidine 1,4-phthalazinediyl diether ((DHQD)2PHAL)-catalyzed chlorocyclization of unsaturated carbamates. Eyring plot analyses of this previously unreported reaction are used to probe and compare the R- and S-selective pathways. In the CHCl3/hexanes solvent system, the pro-R process shows a surprising increase in selectivity with increasing temperature. These studies point to a strongly solvent-dependent entropy-enthalpy balance between the pro-R and pro-S pathways. 
chlorocyclization; enantiodivergence; enantioselectivity; Eyring plots; organocatalysis; oxazolidinones