Totally selective ring-opening of amino epoxides with ketones: A general entry to enantiopure (2R,3S)- and (2S,3S)-3-aminoalkano-1,2-diols

Organic Letters

Volumn 7, Issue 2, 2005, Pages 247-250

  Concellón, José M ^a   Suárez, José Ramón ^a   García Granda, Santiago ^a   Díaz, M Rosario ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ALKANE DERIVATIVE; BORON DERIVATIVE; EPOXIDE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; ENANTIOMER; EPIMERIZATION; RING OPENING;

EID: 13444309394     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047785o     Document Type: Article

References (19)

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17. 4, filtered, and concentrated in vacuo. Flash column chromatography on silica gel (hexane/ EtOAc 20:1) provided pure compounds 2 and 4.
18. CCDC-252205 (2d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ conts/retrieving.html (or the Cambridge Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax (+44)1223-336.033; or deposit@ ccdc.cam.ac.uk).
19. (1′S,4S)-2-(1-aminoalkyl)epoxides 3 were obtained with a diastereoselection ranging from 91% to >98%; see ref 7.