Meyers oxazoline method

What is Meyers oxazoline method?

Chiral oxazolines have been developed by Albert I. Meyers et al., and they have been utilized as activating groups and chiral auxiliaries in nucleophilic addition and substitution reactions.

Meyers oxazoline method- general reaction scheme
Meyers oxazoline method

These reactions are used to construct carbon-carbon bonds in an asymmetric manner. For instance, enantioenriched carboxylic acid 2 can be obtained by metalating chiral oxazoline 1, followed by alkylation and hydrolysis.

Meyers oxazoline method- general reaction scheme
Meyers oxazoline method

Enantioenriched dihydronaphthalenes can also be produced through the addition of alkyllithium reagents to 1-naphthyloxazoline 3, and the resulting anion can be alkylated with an alkyl halide to generate 4.

Reductive cleavage of the oxazoline moiety leads to the formation of aldehyde 5.

In addition, chiral oxazolines have been used as ligands in various asymmetric catalysis applications.

References

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