Highly Enantioselective Intermolecular Iodo- and Chloroamination of Enecarbamates Catalyzed by Chiral Phosphoric Acids or Calcium Phosphate Salts

Abstract

Highly enantio-and diastereoselective vicinal chloro-and iodoamination reaction of enecarbamates catalyzed by chiral phosphoric acids or chiral calcium organophosphates are reported. The approach described herein provides efficient access to cis-chloro and cis-iodoaminals in good yields and excellent enantioselectivities (up to 99% ee). The resulting products are converted readily into highly important trans-azidoaminals.

Diastereo-divergent synthesis of chiral hindered ethers via a synergistic calcium(II)/gold(I) catalyzed cascade hydration/1,4-addition reaction

“…1d). Specifically, we have discovered that chiral BINOL-derived calcium phosphate catalysts [70][71][72][73][74][75][76][77][78][79][80] serve as efficient Lewis acids for the generation and activation of o-QMs. By carefully selecting a suitable chiral Au(I) complex in combination with the chiral calcium phosphate catalyst, we have achieved stereodivergent cascade reactions, providing access to all four stereoisomers of the products (Fig.…”