Kumar Naveen, Nishkant Malkoti, Vishesh Singh Rawat, Prof. Dr. Elumalai Gnanamani
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Diastereoselective Michael Addition of Non-Functionalized Furanone to Nitroalkenes in Aqueous Condition
Selectivity plays a major role in organic chemistry and biological applications. Herein, we present a diastereoselective DMAP-catalyzed Michael addition of furanone (butenolide) to nitroalkenes. Notably, our method does not require the pre-activation of furanone as 2-(trimethylsiloxy)furan and utilizes water: ethanol (1:3) as a solvent. These mild conditions afford the anti-Michael products in up to 82% isolated yield with up to 87:13 dr (diastereomeric ratio). The scope of this reaction extends to various aromatic, heteroaromatic, and aliphatic nitroalkenes. Furthermore, we demonstrate this process on a gram scale and highlight the utility of the obtained Michael adducts for accessing natural product cores.
期刊介绍:
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.