The First Synthesis of Enantiopure α-Amino Ketimines and Amino Aziridines
- 20 March 2001
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (8) , 2764-2768
- https://doi.org/10.1021/jo005741x
Abstract
Chiral 1-aminoalkyl chloromethyl ketimines 2 are synthesized in enantiomerically pure form starting from 1-aminoalkyl chloromethyl ketones 1 and different amines. Reduction of amino ketimines 2 and subsequent spontaneus cyclization affords aminoalkyl aziridines 3 with high diastereoisomeric excess and without detectable racemization.Keywords
This publication has 27 references indexed in Scilit:
- Aza-Darzens Asymmetric Synthesis of N-(p-Toluenesulfinyl)aziridine 2-Carboxylate Esters from Sulfinimines (N-Sulfinyl Imines)The Journal of Organic Chemistry, 1999
- Synthetic Applications of 1-Aminoalkyl Chloromethyl Ketones. Synthesis of Enantiopure 3-Azetidinols and Aminoalkyl EpoxidesThe Journal of Organic Chemistry, 1997
- Asymmetric aziridine synthesis via aza-Darzens reaction of bromoacylcamphorsultamChemical Communications, 1996
- High Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from .alpha.-Amino AcidsThe Journal of Organic Chemistry, 1995
- Reactivity of 2,3-Aziridino-2,3-dideoxy-D-lyxono-.gamma.-lactone Derivatives, Rigid Analogs of Aziridine-2-carboxylic Esters, toward Soft and Hard Nucleophiles: Control of Lactone vs Aziridine Ring Opening and C-2 vs C-3 RegioselectivityThe Journal of Organic Chemistry, 1995
- Carbenoid Transfer to Imines: A New Asymmetric Catalytic Synthesis of AziridinesAngewandte Chemie International Edition in English, 1995
- The first direct preparation of chiral functionalised ketones and their synthetic usesJournal of the Chemical Society, Chemical Communications, 1994
- Acid-Catalyzed Ring Opening of 2-Substituted Aziridines with AlcoholsSynthesis, 1992
- An Overview of the Total Synthesis of Pyrrolizidine Alkaloids via [4 + 1]Azide-Diene Annulation MethodologySynlett, 1990
- Diaminozucker, XI Synthese der 2.3‐Diamino‐2.3‐didesoxy‐D‐galaktoseEuropean Journal of Inorganic Chemistry, 1970