期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 19, 期 27, 页码 9015-9021出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201300189
关键词
chlorocyclization; enantiodivergence; enantioselectivity; Eyring plots; organocatalysis; oxazolidinones
资金
- NSF [CHE-0957462]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0957462] Funding Source: National Science Foundation
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.
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