Enantioselective Total Synthesis of (1R,3S,4R,5R)-1-Amino-4,5-dihydroxycyclopentane-1,3-dicarboxylic Acid. A Full-Aldol Access to Carbaketose Derivatives

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2611-2613

  Battistini, Lucia ^a   Curti, Claudio ^a   Zanardi, Franca ^a   Rassu, Gloria ^b   Auzzas, Luciana ^b   Casiraghi, Giovanni ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DERIVATIVES; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVE SYNTHESIS;

AROMATIC HYDROCARBONS;

1 AMINO 4,5 DIHYDROXYCYCLOPENTANE 1,3 DICARBOXYLIC ACID; 2 HYDROXYMETHYLGLUTAMIC ACID; ALDEHYDE; AMINO ACID; CYCLOPENTANE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; GLUTAMATE RECEPTOR AGONIST; GLUTAMIC ACID DERIVATIVE; LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CATALYSIS; DICARBOXYLIC ACIDS; GLUTAMIC ACID; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; RECEPTORS, METABOTROPIC GLUTAMATE; STEREOISOMERISM;

EID: 1842450692     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035846a     Document Type: Article

References (21)

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15. Presumably, the reaction proceeds via the Diels-Alder-like endo transition structure I, featuring a Felkin-type facial diastereoselectivity (addition of the aldehyde from the re-face). The transition state I then collapses to afford the major 4S,5R-configured adduct 10. Formation of the minor 4R,5R isomer 11, in contrast, would require a high-energy exo transition state II possessing an unfavorable orientation of the aldehyde dioxolanyl substituent. (diagram presented). For a recent theoretical study of the mechanisms of related Lewis acid assisted reactions involving five-membered heterocyclic dienes, see: Yu, Z.-X.; Wu, Y.-D. J. Org. Chem. 2003, 68, 421-432.
16. For this minor isomer, the absolute configuration at C5 could not be firmly assigned.
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19. On standing, this material equilibrated into a 60:40 anomeric mixture.
20. Rassu, G.; Auzzas, L.; Pinna, L.; Zambrano, V.; Zanardi, F.; Battistini, L.; Gaetani, E.; Curti, C.; Casiraghi, G. J. Org. Chem. 2003, 68, 5881-5885 and references therein.
21. A minor 4,5-cis-configured isomer was also isolated and fully characterized (Supporting Information).