@article{MTMT:1413310, title = {Stereoselective synthesis of pinane-based β- and γ-amino acids via conjugate addition of lithium amides and nitromethane}, url = {https://m2.mtmt.hu/api/publication/1413310}, author = {Szakonyi, Zsolt and Balázs, Á and Martinek, Tamás and Fülöp, Ferenc}, doi = {10.1016/j.tetasy.2010.09.009}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {21}, unique-id = {1413310}, issn = {0957-4166}, abstract = {Michael addition of dibenzylamine to (-)- and (+)-tert-butyl myrtenate, (-)-2 and (+)-2, derived from (-)- and (+)-myrtenal, furnished monoterpene-based β-amino acid derivatives in highly stereospecific reactions. The resultant amino esters (-)-3 and (+)-3 were transformed to unsubstituted, mono- and disubstituted and Fmoc-protected amino acids (-)-6-11 and (+)-6-11, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles. The microwave-assisted conjugate addition of nitromethane to α,β-unsaturated esters (-)-12 and (+)-12 likewise resulted in nitro esters (-)-13 and (+)-13 in highly stereospecific reactions. Compounds (-)-13 and (+)-13 were successfully transformed into γ-amino acids (-)-16 and (+)-16 in two steps. © 2010 Elsevier Ltd. All rights reserved.}, keywords = {ARTICLE; LITHIUM; priority journal; synthesis; reaction analysis; conjugation; AMIDE; stereospecificity; microwave radiation; Michael addition; chemical reaction; addition reaction; nitromethane; heterocyclic compound; dibenzylamine; amino acid derivative; terpene; beta amino acid}, year = {2010}, eissn = {1362-511X}, pages = {2498-2504}, orcid-numbers = {Szakonyi, Zsolt/0000-0003-2432-8409; Martinek, Tamás/0000-0003-3168-8066; Fülöp, Ferenc/0000-0003-1066-5287} }