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Published on: May 26, 2019
Grignard reactions of 4-substituted-2-keto-1,3-dioxanes: highly diastereoselective additions controlled by a remote
W F Bailey1, D P Reed, D R Clark
1Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA. bailey@uconn.edu
Abstract:
[see reaction]. The reactions of Grignard reagents with a representative series of simple cis-2-keto-4-substituted-1,3-dioxanes have been investigated. The stereochemical outcome of these highly diastereoselective additions (dr > 90:10) is consonant with Cram's chelate model on the assumption that RMgX coordinates preferentially with the ring oxygen remote from the C(4) substituent.
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