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  • Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas.

Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas.

Journal of the American Chemical Society (2013-01-17)
Mathieu P Lalonde, Meredeth A McGowan, Naomi S Rajapaksa, Eric N Jacobsen
ABSTRACT

A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Thiourea, ReagentPlus®, ≥99.0%
Sigma-Aldrich
Thiourea, ACS reagent, ≥99.0%
Sigma-Aldrich
Thiourea, JIS special grade, ≥98.0%