Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H2NCH2CH[(CH2)nNHMe]NH2 (n = 1–4) from α-Amino Acids: New Agents for Asymmetric Catalysis

Connor Q. Kabes; Jack H. Gunn; Maximilian A. Selbst; Reagan F. Lucas; John A. Gladysz

doi:10.1055/s-0040-1707146

Synthesis, Table of Contents

Synthesis 2020; 52(21): 3277-3285
DOI: 10.1055/s-0040-1707146

special topic

Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H₂NCH₂CH[(CH₂) _n NHMe]NH₂ (n = 1–4) from α-Amino Acids: New Agents for Asymmetric Catalysis

Connor Q. Kabes

,

Jack H. Gunn

,

Maximilian A. Selbst

,

Reagan F. Lucas

,

John A. Gladysz ∗

Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, USA Email: gladysz@mail.chem.tamu.edu

› Author Affiliations

Abstract

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Published as part of the Special Topic Recent Advances in Amide Bond Formation

Abstract

Tris(hydrochloride) adducts of the title compounds are prepared from the inexpensive α-amino acids H₂N(C=O)CH₂CH(NH₂)CO₂H, HO(C=O)(CH₂)_n′CH(NH₂)CO₂H (n′ = 1, 2), and H₂N(CH₂)₄CH(NH₂)CO₂H, respectively (steps/overall yield = 5/32%, 7/30%, 7/33%, 5/38%). The NH₂ group that is remote from the secondary amine is installed via BH₃ reduction of an amide [–(C=O)NR₂] derived from an α-amino carboxylic acid. The MeNHCH₂ units are introduced by BH₃ reductions of alkyl carbamate [RO(C=O)NHCH₂–; R = Et, t-Bu] or amide [MeHN(C=O)–] moieties.

Key words

1,2-diamines - triamines - α-amino acids - chiral ligands - BH₃ reduction - amides - carbamates

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References

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Supplementary Material

Supporting Information

Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H2NCH2CH[(CH2) n NHMe]NH2 (n = 1–4) from α-Amino Acids: New Agents for Asymmetric Catalysis

Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H₂NCH₂CH[(CH₂) _n NHMe]NH₂ (n = 1–4) from α-Amino Acids: New Agents for Asymmetric Catalysis