Synthesis of novel amino squaric acids via addition of dianion enolates derived from N-Boc amino acid esters

Tetrahedron Letters

Volumn 46, Issue 2, 2005, Pages 311-314

  Ishida, Toshikazu ^a   Shinada, Tetsuro ^a   Ohfune, Yasufumi ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Amino acid; Dianion enolate; Squaric acid

Indexed keywords

2 PROPANOL; AMINO ACID DERIVATIVE; CARBOXYLIC ACID; ESTER DERIVATIVE;

ADDITION REACTION; ARTICLE; DECARBOXYLATION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 10044243875     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.044     Document Type: Article

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57. 1H NMR (400 MHz) δ 9.27 (br s, 1H), 8.67 (br s, 1H), 4.44 (br s, 1H), 3.3-3.1 (m, 2H), 1.85-2.20 (m, 4 H)
58. The compound 2e (4-((1R,2S)- and (1S,2S)-1-amino-2-methylbutyl)-3- hydroxycyclobut-3-ene-1,2-dione, [sq-isoleucine])was obtained as an inseparable 5:3 mixture of diastereomers at the carbon attached to the amino group. The absolute stereochemistry at C-1 and C-2 are R/S (5:3 or 3:5) and S, respectively. The integral values of the protons were indicated as a number of observed H/8