Construction of Polycyclic Fused Pyrrolidines with Three Contiguous Stereocenters via Michael Addition of Vinylmalononitriles to Nitrostyrenes­ Using l-Proline-Derived Thiourea

Abstract

The catalytic efficiency of a bifunctional chiral thiourea derived from l-proline was evaluated in the asymmetric direct vinylogous Michael reaction of α,α-dicyanoolefins to β-nitrostyrenes with an electron-releasing or electron-withdrawing substituent in various positions. The corresponding adducts were isolated in good yields, with excellent diastereo- (>99%) and enantioselectivity (up to 95%). The Michael adducts were further functionalized to achieve the synthesis of polycyclic fused pyrrolidines with three contiguous stereocenters in good enantioselectivities.

Key words

asymmetric synthesis - pyrrolidines - Michael addition - organocatalysis - bifunctional thioureas

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