4.7 Article

Modular Stereocontrolled Assembly of R2Zn, Cyclic Enones and N-tert-Butanesulfinyl Imines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 6, Pages 2547-2553

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo802812w

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Funding

  1. Spanish Ministerio de Educacion y Ciencia (MEC) [2010-CSD2007-00006, CTQ-2007-65218]
  2. Spanish MEC

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The assembly of a wide range of dialkylzincs, cyclic enones, and chiral N-tert-butylsulfinyl imines in the presence of the appropriate phosphoramidite ligands allowed the formation of beta-amino ketones with three consecutive stereogenic centers in a stereocontrolled manner. The Baeyer-Villiger oxidation of the resulting amino ketones led to the corresponding aminolactones with excellent regio- and stereoselectivities.

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