Gram-scale synthesis of (+)- and (-)-trans-10-amino-9-hydroxy-9,10-dihydrophenanthrene by enzymatic hydrolysis

Chirality

Volumn 14, Issue 6, 2002, Pages 490-494

  Irurre, J ^a   Riera, M ^a,b   Guixa M ^a  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

^b AALTO UNIVERSITY   (Finland)

Author keywords

Amino alcohols; Hydroxysulphonamides; Kinetic resolution; Lipases

Indexed keywords

10 AMINO 9 HYDROXY 9,10 DIHYDROPHENANTHRENE; AMINOALCOHOL; BENZENESULFONAMIDE DERIVATIVE; PHENANTHRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA; DERIVATIZATION; ENANTIOMER; ENZYME MECHANISM; HYDROLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0036313690     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10075     Document Type: Article

References (29)

1. Enzymatic resolution of bicyclic 1,3-amino alcohols in organic media
2. An efficient synthesis of enantiopure (+)-and (-)-3-exo-amino-7,7-dimethoxynorbornan-2-exo-ols
3. Preparation of (R)-(1-adamantyl) glycine and (R)-2-(1-adamantyl)-2-aminoethanol: A combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution
4. Aminoalcohols. III. Preparation of enantiomerically pure pharmacologically active N-substituted β-aminoalcohols
5. Electrochemical oxidation of chiral 5-substituted 2-oxazolidinones: A key building block for dichiral β-amino alcohols
6. An efficient and practical preparation of optically active syn-1-vinyl-2-amino alcohol derivatives by the regio- and diastereoselective addition reaction of (γ-alkoxyallyl) titaniums with chiral imines. Formal synthesis of statine
7. 1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
8. Chiral induction effects in ruthenium(II) amino alcohol catalyzed asymmetric transfer hydrogenation of ketones: An experimental and theoretical approach
9. Asymmetric reduction of prochiral ketones using in situ generated oxazaborolidines derived from amino alcohols of (1R)-camphor as catalysts
10. A novel and efficient synthesis of (+) and (-)-trans-2-aminocyclohexanol by enzymatic hydrolisis
11. Enzymatic resolutions of cyclic amino alcohol precursors
12. Enzymic preparation of enantiomerically pure (1R,2R)-and (1S,2S)-2-aminocyclohexanols
13. Enzymic resolution of (±)-trans-2-aminocyclohexanol and (±)-trans-2-aminocyclopentanol
14. How large are the active sites of the lipases from Candida rugosa and from Pseudomonas cepacia?
15. A contribution to evaluate the size of the active-site of the lipases from Candida rugosa and Pseudomonas cepacia
16. 6-Deoxiadenosine adducts resulting from cis and trans ring-opening of Phenanthrene 9,10-oxide
17. Synthesis of phenanthrene-9,10-imine tosylate. A stable arene imine
18. Direct peracid oxidation of polynuclear hydrocarbons to arene oxides
19. Derivatives of α,α,α',α'-tetraaryl-2,2-dimethyl-1,3-dioxolane-4, 5-dimethanol (TADDOL) containing nitrogen, sulfur, and phosphorus atoms. New ligands and auxiliaries for enantioselective reactions
20. On the regioselectivity in transformation of Benzo[a]pyrene-4,5-oxide and 3-Methylcholanthrene-11,12-oxide to the corresponding β-amino-alcohol derivatives
21. A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia and lipase from Candida rugosa
22. Stereoselectivity of Pseudomonas cepacia lipase toward secondary alcohols: A quantitative model
23. Enantioselectivity of Candida antarctica lipase for some synthetic substrates including aliphatic secondary alcohols
24. Enantioselective cyclopropanation of allylic alcohols. The effect of zinc iodide
25. Stable arene amines
26. The chemistry of polycyclic arene imines. I. Substitution at the nitrogen atom of 1a,9b-dihydro-1H-phenanthro[9,10-b]azirine