Abstract
AbstractFor the first time we have been able to employ enantiopure 1,2‐amino alcohols derived from abundant amino acids in C−C bond‐forming hydrogen‐borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub‐stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleaved in one pot to give γ‐aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may be performed in sequence without isolation of the hydrogen‐borrowing intermediate, removing the need for column chromatography.
Highlights
For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in CÀC bond-forming hydrogen-borrowing alkylation reactions
An attractive alternative employs hydrogen-borrowing catalysis, which enables alcohols to be used as electrophiles in alkylation reactions with enolates.[3]
We have reported the use of catalytic iridium to enable the alkylation reactions of pentamethylphenyl (Ph*) methyl ketone with a range of primary and secondary alcohols, forming branched products, as well as with diols to form cyclohexanes.[4]
Summary
For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in CÀC bond-forming hydrogen-borrowing alkylation reactions. An attractive alternative employs hydrogen-borrowing catalysis, which enables alcohols to be used as electrophiles in alkylation reactions with enolates.[3] This avoids many of the problems associated with traditional electrophiles, with the additional advantage of water being the only stoichiometric waste product.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
