Journal of the American Chemical Society 2006-01-11

Anion relay chemistry: an effective tactic for diversity oriented synthesis.

Amos B Smith, Ming Xian

Index: J. Am. Chem. Soc. 128 , 66, (2006)

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Abstract

An effective one-flask multicomponent linchpin coupling protocol employing the concept of anion relay chemistry (ARC) was developed. This concept calls for addition of an anion (5) to an epoxide (6), bearing on a distal carbon a trialkyl silyl group and an anion stabilizing group (ASG), to furnish upon epoxide ring opening oxyanion 7. Addition of HMPA or other polar solvents to trigger a solvent controlled 1,4-Brook rearrangement then leads to a new distal anion (8), which in turn is available to react with a variety of second electrophiles.