Efficient syntheses of polyfunctional nitro compounds using 2‐alkenyl‐substituted methyl 2‐siloxycyclopropanecarboxylates as key building blocks

Abstract

Abstract Cyclopropane derivatives as 1 are excellent precursors for vinyl ketones like 2 , which can be used as Michael acceptors in reactions with several nitroalkanes. Efficient preparation of trifunctional, tetrafunctional, and pentafunctional compounds is described. Also, nitroalkane adducts like 15 can serve as Michael donor allowing synthesis of adducts 17, 18 , and 19 , respectively. The construction of these polyfunctional systems with differentiated and masked carbonyl groups is analyzed in terms of the concept of reactivity umpolung.