Asymmetric Synthesis VIII: Enantioselective Synthesis of (R) or (S)-α-Substituted Benzylamines VIA Chiral Pinanone Ketimine Template
- 1 April 1989
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 19 (7) , 1423-1430
- https://doi.org/10.1080/00397918908054552
Abstract
An excellent asymmetric synthesis of both (R) and (S)-α-substituted benzylamines in optical purity 90.4–99.9% has been achieved by alkylation of a chiral ketimine, prepared from pinanone and benzylamine. Diastereoselectivity in the alkylation is not dependent on the alkyl halides.Keywords
This publication has 10 references indexed in Scilit:
- Asymmetric Syntheses IV: Enantioselective Synthesis of (R)-Benzylic Amines Via Alkylation of D-Camphor KetimineSynthetic Communications, 1987
- A Convenieni Catalytic System of Potassium Carbonate and Alkanol: The Michael Addition and Carbonyl Addition Reactions of Imine CompoundsSynthetic Communications, 1987
- Synthese stereospecifique de l'ester methylique de l'acide amino-2 oxo-8 epoxy-9,10 decanoique (2s,9r) N - protege.Tetrahedron Letters, 1984
- Synthese asymetrique d'acides amines α-disubstituesTetrahedron Letters, 1983
- Amino acids and peptides. XXIX. A new efficient asymmetric synthesis of .ALPHA.-amino acid derivatives with recycle of a chiral reagent - asymmetric alkylation of a chiral Schiff base from glycine.CHEMICAL & PHARMACEUTICAL BULLETIN, 1978
- Optically active amines. XVII. Partial kinetic resolution of .alpha.-phenylbutyric acid using chiral primary amines and their saltsThe Journal of Organic Chemistry, 1974
- Synthesis and stereochemistry of the four isomeric pinane-2,3-diolsThe Journal of Organic Chemistry, 1971
- Optically active amines. XI. Optical rotatory dispersion and circular dichroism observations on .alpha.- and .beta.-phenylalkylamine hydrochloridesJournal of the American Chemical Society, 1971
- The reduction of oximes with tervalent titanium, a mild deoximation procedure and the partial synthesis of erythromycylamine.Tetrahedron Letters, 1971
- Optically Active Amines. III. The Optical Rotatory Dispersion Curves of the N-Salicylidene Derivatives of Some Open-Chain Primary Amines1Journal of the American Chemical Society, 1965