An asymmetric synthesis of (R)- or (S)- azatyrosine, starting from (2S)- or (2R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (5) (Schöllkopf reagent) and 5-benzenesulfonyloxy-2-hydroxymethylpyridine (3), is reported. The diastereocontrolled addition gives mainly one of two possible adducts with the (2S, 5R) or (2R, 5S) configuration respectively. After the removal of the chiral auxiliary and benzenesulfonyloxy group, azatyrosine is obtained in good yields and high ee.
A stereocontrolled synthesis of (R)- and (S)-Azatyrosine / G. Cremonesi, P. Dalla Croce, C. La Rosa, E. Pizzatti. - In: HETEROCYCLES. - ISSN 0385-5414. - 61:1(2003), pp. 563-567.
A stereocontrolled synthesis of (R)- and (S)-Azatyrosine
G. CremonesiPrimo
;P. Dalla CroceSecondo
;C. La RosaPenultimo
;
2003
Abstract
An asymmetric synthesis of (R)- or (S)- azatyrosine, starting from (2S)- or (2R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (5) (Schöllkopf reagent) and 5-benzenesulfonyloxy-2-hydroxymethylpyridine (3), is reported. The diastereocontrolled addition gives mainly one of two possible adducts with the (2S, 5R) or (2R, 5S) configuration respectively. After the removal of the chiral auxiliary and benzenesulfonyloxy group, azatyrosine is obtained in good yields and high ee.
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