The Asymmetric Birch Reduction and Reduction–Alkylation

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The asymmetric Birch reduction and reduction–alkylation strategies for
synthesis of natural products
Arthur G. Schultz

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Abstract

Synthetic applications of the asymmetric Birch reduction and
reduction–alkylation are reported. Synthetically useful chiral
intermediates have been obtained from chiral 2-alkoxy-,
2-alkyl-, 2-aryl- and 2-trialkylsilyl-benzamides I and the
pyrrolobenzodiazepine-5,11-diones II. The availability of a wide
range of substituents on the precursor benzoic acid derivative,
the uniformly high degree of diastereoselection in the chiral
enolate alkylation step, and the opportunity for further
development of stereogenic centers by way of olefin addition
reactions make this method unusually versatile for the asymmetric
synthesis of natural products and related materials.