α′-Benzoyloxy and α′-methoxymethoxy lithium enolates giving opposite diastereofacial selectivities in aldol reactions. Use of (probable) extended chelation for reversal of stereoselectivities
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Add time:08/19/2019 Source:sciencedirect.com
The Li enolates of α-benzoyloxy and α-methoxymethoxy ketones 1a and 1c afford nonchelation and chelation aldol products, respectively, both with usefully high diastereofacial selectivities. Evidence suggests that transition state chelation of the benzoyl C=O is responsible for the observed “nonchelation” stereoselectivity of 1a.
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