Scope of stereoselective Mn-mediated radical addition to chiral hydrazones and application in a formal synthesis of quinine

…, A Ji, J Baltrusaitis, CS Korapala, J Qin

Index: Friestad, Gregory K.; Ji, An; Baltrusaitis, Jonas; Korapala, Chandra Sekhar; Qin, Jun Journal of Organic Chemistry, 2012 , vol. 77, # 7 p. 3159 - 3180

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Citation Number: 15

Abstract

Stereocontrolled Mn-mediated addition of alkyl iodides to chiral N-acylhydrazones enables strategic C–C bond constructions at the stereogenic centers of chiral amines. Applying this strategy to quinine suggested complementary synthetic approaches to construct C–C bonds attached at the nitrogen-bearing stereogenic center using multifunctional alkyl iodides 6a–d as radical precursors, or using multifunctional chiral N-acylhydrazones 26a–d as radical ...

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