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Synthesis 2020; 52(21): 3277-3285
DOI: 10.1055/s-0040-1707146
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
The authors thank the Welch Foundation (Grant A-1656) for support.Further Information
Publication History
Received: 04 May 2020
Accepted after revision: 18 May 2020
Publication Date:
16 June 2020 (online)
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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 - carbamatesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707146.
- Supporting Information
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