Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

Carswell, Emma L. and Kerr, William J and McArthur, Duncan and Pazicky, Marek and Watson, Allan (2014) Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates. Tetrahedron, 70 (40). pp. 7344-7349. ISSN 0040-4020 (https://doi.org/10.1016/j.tet.2014.06.052)

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Abstract

A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An effective complex was identified and applied within enantioselective enolisation processes, delivering good levels of enantioselectivity and also revealing key structural requirements for achieving such selectivity.