Evans auxiliary-based asymmetric synthesis

E634404

Evans auxiliary-based asymmetric synthesis is a widely influential chiral auxiliary strategy developed by David A. Evans that enables highly stereoselective construction of complex molecules in organic synthesis.

All labels observed (2)

How this entity was disambiguated

Statements (49)

Predicate Object
instanceOf asymmetric synthesis strategy ⓘ
chiral auxiliary methodology ⓘ
stereoselective synthesis method ⓘ
advantage auxiliary can be removed after stereocenter formation ⓘ
auxiliary can often be recovered and reused ⓘ
appliedIn complex molecule construction ⓘ
pharmaceutical synthesis ⓘ
total synthesis of natural products ⓘ
basedOn chiral N-acyl oxazolidinone auxiliaries ⓘ
contrastsWith catalytic asymmetric synthesis ⓘ
controls relative configuration of newly formed stereocenters ⓘ
developedBy David A. Evans ⓘ
enables highly stereoselective construction of complex molecules ⓘ
field organic chemistry ⓘ
synthetic organic chemistry ⓘ
followedBy auxiliary cleavage to reveal enantiomerically enriched products ⓘ
historicalImpact popularized chiral auxiliary approach in asymmetric synthesis ⓘ
influenced development of other chiral auxiliary systems ⓘ
involves diastereoselective bond formation ⓘ
enolization under basic conditions ⓘ
formation of N-acyl imides ⓘ
keyIntermediate chiral metal enolate ⓘ
keyTransformation diastereoselective Michael addition ⓘ
keyTransformation diastereoselective acylation ⓘ
diastereoselective conjugate addition ⓘ
keyTransformation diastereoselective aldol reaction ⓘ
keyTransformation diastereoselective enolate alkylation ⓘ
namedAfter David A. Evans ⓘ
optimizationParameter choice of base and metal counterion ⓘ
temperature control for stereoselectivity ⓘ
provides high diastereoselectivity ⓘ
predictable stereochemical outcome ⓘ
reliesOn chelation-controlled transition states ⓘ
diastereofacial differentiation of enolates ⓘ
requires stoichiometric amount of chiral auxiliary ⓘ
stereochemicalOutcome products with high enantiomeric excess after auxiliary removal ⓘ
stereocontrolOrigin chiral environment of the oxazolidinone ring ⓘ
strategyType substrate-controlled stereoselective synthesis ⓘ
timePeriodOfDevelopment 1980s ⓘ
late 1970s ⓘ
typicalAuxiliaryBackbone oxazolidinone derived from amino alcohols ⓘ
typicalMetalCounterion boron ⓘ
lithium ⓘ
titanium ⓘ
typicalSubstrateClass chiral N-acyl oxazolidinones ⓘ
usedFor construction of contiguous stereocenters ⓘ
construction of quaternary stereocenters ⓘ
uses Evans chiral auxiliary ⓘ
N-acyloxazolidinone chiral auxiliaries ⓘ

How these facts were elicited

Referenced by (3)

Full triples — surface form annotated when it differs from this entity's canonical label.

David A. Evans → notableWork → Evans auxiliary-based asymmetric synthesis ⓘ
Evans auxiliary-based asymmetric synthesis → uses → Evans chiral auxiliary ⓘ
linked to: Evans auxiliary-based asymmetric synthesis
Evans aldol reaction → usesAuxiliary → Evans chiral auxiliary ⓘ
linked to: Evans auxiliary-based asymmetric synthesis