C2‐Symmetrical Pyrrolidine Derivatives Chiral Auxiliaries in Radical Chemistry
- 10 February 1993
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 76 (1) , 441-450
- https://doi.org/10.1002/hlca.19930760128
Abstract
Fumaramides 3b and 3c bearing the C2‐symmetrical pyrrolidine moieties (2R,5R)‐2,5‐bis(methoxymethyl)pyrrolidine (2b) or 1,3:4,6‐di‐O‐benzylidene‐2,5‐dideoxy‐2,5‐imino‐L‐idit (2c), respectively, as a chiral auxiliary lead to high diastereoselectivities in radical reactions (‘tin method’;Scheme 1). Removal of the chiral auxiliaries affords the corresponding alkylated fumaric acids Scheme 2. Single‐crystal X‐ray structures of 3b and 3c support arguments that lead to the model of 1,4‐stereoinduction.Keywords
This publication has 13 references indexed in Scilit:
- Competition rate constants for addition of cyclohexyl radical to amide substituted alkenes: origins of acyclic stereoselection in radical additionsTetrahedron Letters, 1991
- Stereoselective intermolecular radical additions to amide-substituted alkenesJournal of the American Chemical Society, 1991
- AsymmetricDiels-Alder Cycloadditions withC2-Symmetrical Chiral Carbamoylnitroso DienophilesHelvetica Chimica Acta, 1991
- Chiroptical properties and molecular geometry of substituted succinic anhydrides and imidesJournal of the Chemical Society, Perkin Transactions 1, 1988
- Syntheses with Radicals—C-C Bond Formation via Organotin and Organomercury Compounds [New Synthetic Methods (52)]Angewandte Chemie International Edition in English, 1985
- Asymmetric alkylation of carboxyamides by using trans-2,5-disubstituted pyrrolidines as chiral auxiliariesTetrahedron Letters, 1984
- Preparative Scale Directed Resolution of Enantiomeric Carboxylic Acids and Lactones via Liquid Chromatography and Neighboring‐Group Assisted Hydrolysis of Diastereomeric AmidesAngewandte Chemie International Edition in English, 1979
- Die Addition von Kohlenwasserstoffen an Olefine Eine neue synthetische MethodeEuropean Journal of Inorganic Chemistry, 1977
- IR and NMR studies on the conformation of α,β-unsaturated N,N-dimethylamides. The carbonyl stretch vibration in relation to the conformationSpectrochimica Acta Part A: Molecular Spectroscopy, 1971
- Etude des systèmes binaires contenant les antipodes des acides phénylsuccinique et cyclohexylsucciniqueBulletin des Sociétés Chimiques Belges, 1953