A general synthesis of unnatural α-amino acids by iron-catalysed olefin–olefin coupling via generated radicals
Literature Information
Publication Date
2019-02-18
DOI
10.1039/C9QO00108E
Impact Factor
5.281
Authors
Nadezhda V. Stoletova, Vladislav I. Kovalev, Tat'yana F. Savel'yeva, Victor I. Maleev
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Abstract
Herein, we report an efficient and practical protocol for the asymmetric synthesis of unnatural α-amino acids (AAs) with γ-tertiary and quaternary carbon centres via selective intermolecular iron-catalysed olefin–olefin coupling of a chiral Ni(II) complex of dehydroalanine Schiff base 2 ((S)-BPB-Ni-Δ-Ala) with different olefins. In all successful reactions, diastereomeric nickel complexes were typically obtained in a ratio of up to dr > 20 : 1. The desired products were isolated in 42–93% yields (18 examples). Exemplarily, the three Ni(II) complexes obtained were decomposed with aqueous HCl and the target unnatural α-amino acids were isolated with excellent enantioselectivities and yields of up to 83%. The chiral auxiliary (BPB = 2-(N-benzylprolyl)aminobenzophenone) was readily recycled and reused for the synthesis of the starting chiral Ni(II) complex 2. The developed protocol provided a facile access to the analogues of glutamic acid, leucine and phosphinothricin.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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[3-(2,6-Dichlorophenyl)-5-isopropyl-1,2-oxazol-4-yl]methanol
CAS Number:
278597-30-1
Molecular Formula:
C13H13Cl2NO2
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403661-85-8
Molecular Formula:
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Molecular Formula:
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