Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective

• Yaroslav D. Boyko,
• Valentin S. Dorokhov,
• Alexey Yu. Sukhorukov and
• Sema L. Ioffe

Beilstein J. Org. Chem. 2017, 13, 2214–2234, doi:10.3762/bjoc.13.220

• 10.3762/bjoc.13.220 Abstract Despite of their chemical instability and high reactivity, conjugated nitrosoalkenes are useful intermediates in target-oriented organic synthesis. The present review deals with carbon–carbon bond forming reactions involving Michael addition to α-nitrosoalkenes with a

• particular focus on recent developments in this methodology and its use in total synthesis. Keywords: carbon–carbon bond formation; Michael addition; nitrosoalkenes; oximes; total synthesis; Introduction Conjugated nitrosoalkenes (NSA) are close analogs of α-nitroalkenes, which are important Michael

• acceptors in organic synthesis [1][2][3][4][5]. Unlike the parent α-nitroalkenes, α-nitrosoalkenes are unstable species usually generated in situ, and their synthetic potential has been studied in significantly less detail [6][7]. Because of relatively short lifetimes of α-nitrosoalkenes, conjugate addition