Lithium
Amino Alkoxide–Evans Enolate Mixed
Aggregates: Aldol Addition with Matched and Mismatched Stereocontrol
Posted on 2018-02-19 - 05:36
Building
on structural and mechanistic studies of lithiated enolates
derived from acylated oxazolidinones (Evans enolates) and chiral lithiated
amino alkoxides, we found that amino alkoxides amplify the enantioselectivity
of aldol additions. The pairing of enantiomeric series affords matched
and mismatched stereoselectivities. The structures of mixed tetramers
showing 2:2 and 3:1 (alkoxide-rich) stoichiometries are determined
spectroscopically. Rate and computational studies provide a viable
mechanistic and stereochemical model based on the direct reaction
of the 3:1 mixed tetramers, but they raise unanswered questions for
the 2:2 mixed aggregates.
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Jermaks, Janis; Tallmadge, Evan H.; Keresztes, Ivan; Collum, David B. (2018). Lithium
Amino Alkoxide–Evans Enolate Mixed
Aggregates: Aldol Addition with Matched and Mismatched Stereocontrol. ACS Publications. Collection. https://doi.org/10.1021/jacs.7b13776
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AUTHORS (4)
JJ
Janis Jermaks
ET
Evan H. Tallmadge
IK
Ivan Keresztes
DC
David B. Collum
KEYWORDS
enantioselectivitylithiated enolatesacylated oxazolidinonesaggregatealkoxidealkoxide-richLithiumpairingchiral lithiatedEvans enolatesstoichiometriestereoselectivitieMismatched Stereocontrol BuildingAggregatestereochemical modelAldol AdditionMatchedMixedtetrameraldol additionsAlkoxideEnolateenantiomeric seriesspectroscopicallyAmino