Highly Diastereoselective and Enantioselective Addition of Organometallic Reagents to a Chiral C ₂-Symmetrical Bisimine

Abstract

An efficient and straightforward method has been developed for the preparation of enantiomerically enriched C ₂-symmetrical vicinal diamines via the addition of organometallic reagents to a chiral bisimine, which gives access to a variety of optically pure ­aromatic and aliphatic C ₂-symmetrical vicinal diamines in high yields. The ‘Cram-Davis’ open transition state model is proposed to rationalize the observed stereoselectivities for the addition of ­organolithium reagents to the bisimine.

chiral 1,2-diamine - chiral bisimine - asymmetric addition - organometallic reagents - asymmetric allylation

References

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Procedure for the Synthesis of Bisimine 2.
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