Journal
TETRAHEDRON-ASYMMETRY
Volume 19, Issue 22, Pages 2563-2567Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2008.10.033
Keywords
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Funding
- National Science Foundation (NSF) [CHE 644950]
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The stereochemical outcome of the asymmetric addition of diethylzinc to aldehydes catalyzed by (R,R)-hydrobenzoin can be influenced by the absence or presence of Ti(O-iPr)(4). The enantiomeric ratios obtained in the absence of Ti(O-iPr)(4) favor the (S)-enantiomer, whereas the ratios obtained from the use of Ti(O-iPr)(4) favor the formation of the (R)-enantiomer. The formation of the opposite enantiomers is attributed to the different transition states mediated by either zinc or titanium. (C) 2008 Elsevier Ltd. All rights reserved.
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