Asymmetric Michael Additions to Nitroalkenes

TLDR

The study presents asymmetric conjugate additions of diverse nucleophiles to nitroalkenes to build highly functionalized synthetic building blocks. The methodology includes diastereoselective, substrate‑controlled 1,4‑additions, auxiliary‑controlled asymmetric Michael additions, external asymmetric variants using enantiopure additives or leaving groups, and catalytic asymmetric syntheses. These reactions enable highly useful C–C and C–X bond formations and subsequent transformations, as demonstrated by multiple applications. © Wiley‑VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Abstract

The asymmetric conjugate addition of various carbon and heteroatom nucleophiles to nitroalkenes as a tool for the construction of highly functionalized synthetic building blocks is presented. Diastereoselective, substrate-controlled 1,4-additions are also included. Besides auxiliary controlled asymmetric Michael additions, external asymmetric versions employing enantiopure additives, addition-elimination processes with enantiopure leaving groups, and catalytic asymmetric syntheses are described. The use of the highly reactive nitroalkenes as Michael acceptors opens the way to synthetically very useful C−C and C−X bond-forming reactions and subsequent transformations as is demonstrated by various applications. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)