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Asymmetric Synthesis of Alpha-Amino Acid Benzyl Esters via the Bisbenzyl Bislactim Ether of cyclo(-L-Val-Gly-)

Asymmetric Synthesis of Alpha-Amino Acid Benzyl Esters via the Bisbenzyl Bislactim Ether of cyclo(-L-Val-Gly-)

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GROTH, Ulrich, Carsten SCHMECK, Ulrich SCHÖLLKOPF, 1993. Asymmetric Synthesis of Alpha-Amino Acid Benzyl Esters via the Bisbenzyl Bislactim Ether of cyclo(-L-Val-Gly-). In: Liebigs Annalen der Chemie. 1993(3), pp. 321-323. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199319930153

@article{Groth1993Asymm-9926, title={Asymmetric Synthesis of Alpha-Amino Acid Benzyl Esters via the Bisbenzyl Bislactim Ether of cyclo(-L-Val-Gly-)}, year={1993}, doi={10.1002/jlac.199319930153}, number={3}, volume={1993}, issn={0170-2041}, journal={Liebigs Annalen der Chemie}, pages={321--323}, author={Groth, Ulrich and Schmeck, Carsten and Schöllkopf, Ulrich} }

Schöllkopf, Ulrich application/pdf Groth, Ulrich 1993 Schmeck, Carsten eng First publ. in: Liebigs Annalen der Chemie 1993, 3, pp. 321-323 2011-03-24T18:15:22Z Schöllkopf, Ulrich Asymmetric Synthesis of Alpha-Amino Acid Benzyl Esters via the Bisbenzyl Bislactim Ether of cyclo(-L-Val-Gly-) Groth, Ulrich 2011-03-24T18:15:22Z Schmeck, Carsten The diketopiperazine cyclo(-L-Val-Gly-) (1) can be 0-alkylated under mild acidic reaction conditions with the alkyl trichloroacetimidates 2 to the corresponding bisalkyl bislactim ethers. Alkylation of the bisbenzyl bislactim ether anion of cyclo(-L-Val-Gly-) 4 c with benzyl bromide and subsequent hydrolysis with aqueous trifluoroacetic acid afforded D-phenyl-alanine benzyl ester (8) with an enantiomeric excess of >95%. deposit-license

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