Continuous-flow enzymatic resolution strategy for the acylation of amino alcohols with a remote stereogenic centre: synthesis of calycotomine enantiomers
作者： László Schönstein , Enikő Forró , Ferenc Fülöp , None
DOI: 10.1016/J.TETASY.2013.01.006
关键词:
摘要: Abstract Both enantiomers of calycotomine ( R )- 5 and S were prepared through the CAL-B-catalysed asymmetric O-acylation N -Boc-protected (6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methanol [(±)- 3 )]. The optimum conditions for enzymatic resolution determined under continuous-flow conditions, while preparative-scale (±)- was performed as a batch reaction with high enantioselectivity E >200). resulting amino alcohol ester 4 , obtained enantiomeric excess ee = 99%), transformed into desired = 99%). A systematic study carried out in system on tetrahydroisoquinoline homologues 1 to containing remote stereogenic centre.
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