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Enantioselective synthesis of planar-chiral 1,n-dioxa[n]paracyclophanes via catalytic asymmetric ortho-lithiation

, : Enantioselective synthesis of planar-chiral 1,n-dioxa[n]paracyclophanes via catalytic asymmetric ortho-lithiation. Organic Letters 12(9): 1980-1983

Highly enantioselective ortho-lithiation and dilithiation of 1,n-dioxa[n]paracyclophanes were realized with the use of sec-butyllithium and a catalytic or stoichiometric amount of sparteine. Quenching with various electrophiles, such as iodine, iodomethane, and chlorodiphenylphosphine, afforded chiral mono- and disubstituted paracyclophanes with good to excellent ee.


PMID: 20349947

DOI: 10.1021/ol100444u

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