Synthesis of orthogonally protected optically pure β-amino acids: Constrained phenylalanine analogs 3-tert-butoxycarbonylamino-1,2,3,4- tetrahydro-2-naphthoic acid benzyl ester

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2271-2274

  Kawahata, Noriyuki H ^a   Goodman, Murray ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Amino acids and derivatives; Aziridines; Samarium and compounds; X ray crystal structures

Indexed keywords

3 TERT BUTOXYCARBONYLAMINO 1,2,3,4 TETRAHYDRO 2 NAPHTHOIC ACID BENZYL ESTER; BETA AMINO ACID; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CRYSTALLOGRAPHY; ISOMERISM; SEQUENCE ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0033583146     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00205-1     Document Type: Article

References (21)

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16. 1H-NMR and the methylene protons (dd centered about δ 4.4 ppm) adjacent to the epoxide and the ester were for comparison.
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19. +) 382.2018, found m / z 382.2004.
20. [10] The X-ray crystallographic data have been deposited in the Cambridge Crystallographic Database.
21. [11] The (2R,3S)-Boc-βAtc-OBn (12a) and (2S,3S) Boc-βAtc-OBn (12b) stereoisomers were obtained from the enantiomer of epoxide (4) which was derived from the use of (-)-diethyltartrate in the catalytic mixture. The syntheses of the dipeptide Boc-Tyr(OtBu)-βAtc-OBn using the four stereoisomers of Boc-βAtc-OBn resulted in four spectroscopically distinct products in high diastereomeric purity. These results provide further evidence that the aziridine ring opening reaction results in single cis and single trans stereoisomers.