Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions of Nitroalkenes. Asymmetric Synthesis of Highly Functionalized Aminocyclopentanes Using the Bridged Mode (β-Tether) Process
- 21 August 1998
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 63 (18) , 6178-6195
- https://doi.org/10.1021/jo9802170
Abstract
An asymmetric, tandem inter [4 + 2]/intra [3 + 2] bridged mode (β-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.Keywords
This publication has 71 references indexed in Scilit:
- Asymmetric Construction of a Quaternary Carbon Center by Tandem [4 + 2]/[3 + 2] Cycloaddition of a Nitroalkene. The Total Synthesis of (−)-MesembrineThe Journal of Organic Chemistry, 1997
- A (1.fwdarw.4)-"trehazoloid" glucosidase inhibitor with aglycon selectivityJournal of the American Chemical Society, 1994
- Enantioselective Synthesis of (1R,4S)-1-Amino-4-(hydroxymethyl)-2-cyclopentene, a Precursor for Carbocyclic Nucleoside SynthesisThe Journal of Organic Chemistry, 1994
- Catalytic asymmetric Diels Alder reactionsChemical Reviews, 1992
- Structure of trehalostatin: a potent and specific inhibitor of trehalaseJournal of the Chemical Society, Chemical Communications, 1991
- Potent and selective activity of a new carbocyclic nucleoside analog (Carbovir: NSC 614846) against human immunodeficiency virus In vitroBiochemical and Biophysical Research Communications, 1988
- INHIBITORS OF THE BIOSYNTHESIS AND PROCESSING OF N-LINKED OLIGOSACCHARIDE CHAINSAnnual Review of Biochemistry, 1987
- High pressure NMR kinetics. Part 22. Mechanism of dimethyl sulfide intermolecular exchange and trans-cis isomerization of tin tetrachloride-2 dimethyl sulfide (SnCl4.cntdot.2Me2S). Variable-pressure proton NMR and variable-temperature tin-119 magnetization transfer NMR studiesInorganic Chemistry, 1985
- Photodimerization of Lewis acid complexes of cinnamate esters in solution and the solid stateJournal of the American Chemical Society, 1984
- 9-[β-DL-2α,3α-Dihydroxy-4β-(hydroxymethyl)- cyclopentyl]adenine, the Carbocyclic Analog of Adenosine1,2Journal of the American Chemical Society, 1966