000013390 001__ 13390
000013390 005__ 20251007025656.0
000013390 02470 $$ahttps://doi.org/10.1021/ja510135t$$2doi
000013390 037__ $$aTEXTUAL
000013390 037__ $$bArticle
000013390 041__ $$aeng
000013390 245__ $$aSynthesis of α-Amino Acid Derivatives and Peptides via Enantioselective Addition of Masked Acyl Cyanides to Imines
000013390 269__ $$a2014-11-07
000013390 336__ $$aArticle
000013390 520__ $$aA general, asymmetric synthesis of amino acid derivatives is reported. Masked acyl cyanide (MAC) reagents are shown to be effective umpolung synthons for enantioselective additions to N-Boc-aldimines. The reactions are catalyzed by a modified cinchona alkaloid, which can function as a bifunctional, hydrogen bonding catalyst, and afford adducts in excellent yields (90–98%) and high enantioselectivities (up to 97.5:2.5 er). Unmasking the addition products gives acyl cyanide intermediates that are intercepted by a variety of nucleophiles to afford α-amino acid derivatives. Notably, the methodology provides an alternative method for peptide bond formation.
000013390 536__ $$oNational Institutes of Health$$cR01GM069990
000013390 540__ $$a<p>© 2014 American Chemical Society</p> <p>This is an open access article published under a Creative Commons Non-Commercial NoDerivative Works (CC-BY-NC-ND) Attribution <a href="http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html">License</a>, which permits copying andredistribution of the article, and creation of adaptations, all for non-commercial purposes.</p>
000013390 542__ $$fCC BY-NC-ND
000013390 690__ $$aPhysical Sciences Division
000013390 691__ $$aChemistry
000013390 7001_ $$aYang, Kin S.$$uUniversity of Chicago
000013390 7001_ $$aRawal, Viresh H.$$uUniversity of Chicago
000013390 773__ $$tJournal of the American Chemical Society
000013390 8564_ $$yArticle$$9cdec6b02-02cf-45d6-8e98-ff12b828aabb$$s911680$$uhttps://knowledge.uchicago.edu/record/13390/files/yang-rawal-2014-synthesis-of-%CE%B1-amino-acid-derivatives-and-peptides-via-enantioselective-addition-of-masked-acyl.pdf$$ePublic
000013390 8564_ $$ySupporting information$$98b1de5d9-3e6a-4889-a927-ccd6c18ef17d$$s5138333$$uhttps://knowledge.uchicago.edu/record/13390/files/ja510135t_si_001.pdf$$ePublic
000013390 908__ $$aI agree
000013390 909CO $$ooai:uchicago.tind.io:13390$$pGLOBAL_SET
000013390 983__ $$aArticle