1268240-77-2Relevant academic research and scientific papers
Benzylation of Imines with Activated Boronate Nucleophiles
Hollerbach, Michael R.,Hayes, Jacob C.,Barker, Timothy J.
supporting information, p. 1646 - 1648 (2019/02/07)
Benzylation reactions of N-tosylimines and N-tert-butanesulfinyl imines using benzylboronic acid pinacol ester are reported. s-Butyllithium was used to activate the boronic ester, rendering it nucleophilic. The reaction was compatible with electronically
Highly Selective Addition of a Broad Spectrum of Trimethylsilane Pro-nucleophiles to N-tert-Butanesulfinyl Imines
Das, Manas,O'Shea, Donal F.
supporting information, p. 18717 - 18723 (2016/01/25)
Addition of organotrimethylsilane reagents to chiral N-tert-butanesulfinyl imines can be achieved in good yields and with excellent diastereoselectivities by employing TMSO-/Bu4N+ as a Lewis base activator in THF. A variety of aliphatic, aromatic, heteroaromatic and organometallic chiral imines were utilised as electrophiles for the synthesis of enantioenriched N-tert-butanesulfinyl amides. Remarkably, the same sets of reaction conditions could be used with a highly diverse range of bench-stable organotrimethylsilane reagents, which highlights the generality and robustness of this methodology. Addition of organotrimethylsilane reagents to chiral N-tert-butanesulfinyl imines can be achieved in good yields and with excellent diastereoselectivities by employing TMSO-/Bu4N+ as a Lewis base activator in THF. A variety of aliphatic, aromatic, heteroaromatic and organometallic chiral imines were utilised as electrophiles for the synthesis of enantioenriched N-tert-butanesulfinyl amides, highlighting the generality and robustness of this methodology.
Asymmetric synthesis of amines by the knochel-type MgCl2- enhanced addition of benzyl zinc reagents to N -tert -Butanesulfinyl aldimines
Buesking, Andrew W.,Baguley, Tyler D.,Ellman, Jonathan A.
supporting information; experimental part, p. 964 - 967 (2011/04/26)
The MgCl2-enhanced addition of benzyl zinc reagents to N-tert-butanesulfinyl imines proceeds readily at room temperature to afford the N-tert-butanesulfinyl-protected amine products in good yields and diastereomeric ratios. This method is functional group tolerant in both the imine substrate and benzyl zinc coupling partner. Moreover, benzyl zinc reagent addition to the N-tert-butanesulfinyl imine 3o prepared from isopropylidene-protected glyceraldehyde proceeds in high yield and with exceptional selectivity to provide rapid entry to hydroxyethylamine-based aspartyl protease inhibitors.(Figure Presented)
