ArticleNature protocols2013
Asymmetric synthesis of amines using tert-butanesulfinamide.
Article in Nature protocols, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 49 citations in OpenAlex.
- Modular Access to α-Tertiary Amines: Electrochemical Tandem Di-Functionalization of Olefins With Ammonia Surrogates and Amino Acids.Angewandte Chemie (International ed. in English) · 2026Article
- Modular synthesis of bis-α-chiral amines using Ellman sulfinamide for consecutiveScience advances · 2025Article
- Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds.Chemical reviews · 2020Article
- A reductive aminase from Aspergillus oryzae.Nature chemistry · 2017Article
- Study on the noncoincidence effect phenomenon using matrix isolated Raman spectra and the proposed structural organization model of acetone in condense phase.Scientific reports · 2017Article
- Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics.Beilstein journal of organic chemistry · 2017Article
- Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Chemoselective amination of propargylic C(sp³)-H bonds by cobalt(II)-based metalloradical catalysis.Angewandte Chemie (International ed. in English) · 2014Article
- Synthesis of diarylmethylaminesChemical science · 2014Article
- Ligand-controlled asymmetric arylation of aliphatic α-amino anion equivalents.Journal of the American Chemical Society · 2014Article
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Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chiral amines are prevalent in many bioactive molecules, including amino acids and pharmaceutical agents. tert-Butanesulfinamide (tBS) is a chiral amine reagent that has enabled the reliable asymmetric synthesis of a very broad range of different amine structures from simple, readily available starting materials. Three steps are commonly applied to the asymmetric synthesis of amines: (i) condensation of tBS with a carbonyl compound, (ii) nucleophile addition and (iii) tert-butanesulfinyl group cleavage. Here we demonstrate these steps with the preparation of a propargylic tertiary carbinamine, one of a class of amines that have been used for many different biological purposes, including click chemistry applications, diversity-oriented synthesis, the preparation of peptide isosteres and the development of protease inhibitors as drug candidates and imaging agents. The process described here can be performed in 3-4 d.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.