Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions of Nitroalkenes. Asymmetric Synthesis of Highly Functionalized Aminocyclopentanes Using the Bridged Mode (β-Tether) Process
Citations Over TimeTop 10% of 1998 papers
Abstract
An asymmetric, tandem inter [4 + 2]/intra [3 + 2] bridged mode (beta-tether) cycloaddition of nitroalkenes has been developed. This new sequence involves the Lewis acid-promoted [4 + 2] cycloaddition of nitro olefins with enantiopure 1-alkoxy-1,4-dienes. The resulting nitronates, bearing a C(5) tethered dipolarophile, undergo thermal, intramolecular [3 + 2] cycloaddition to afford stable tricyclic nitroso acetals, which can be subsequently reduced to provide interesting aminocyclopentanes. Thus, in three steps, highly functionalized, enantiomerically enriched aminocyclopentanes can be constructed with good yield and high ee. Additionally, the Lewis acid was found to impart a remarkable influence on the stereochemical outcome of the [4 + 2] cycloaddition.
Related Papers
- → Photooxidation of 4-chloroaniline and N-(4-chlorophenyl)-benzenesulfonamide to nitroso- and nitro-products(1983)20 cited
- → Nitrosation of alkenes by nitric oxide: Crystal structures of bis-(1-nitroso-2-nitro-cyclohexane) and bis-(1-nitroso-2-nitro-1-phenylethane)(1985)10 cited
- → Hydrogen Bonding and Complex Formation Involving Compounds with Amino, Nitroso and Nitro Groups(2009)3 cited
- → The chemistry of functional groups. Supplement F. Amino, nitroso and nitro compounds and their derivatives(1983)
- → Synthesis of Nitroso, Nitro, and Related Compounds(2023)