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Ir-catalyzed allylic amination/ring-closing metathesis: A new route to enantioselective synthesis of cyclic β-amino alcohol derivatives

Title
Ir-catalyzed allylic amination/ring-closing metathesis: A new route to enantioselective synthesis of cyclic β-amino alcohol derivatives
Authors
Jun H.L.Shin S.Kang J.Lee S.-G.
Ewha Authors
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SCOPUS Author ID
이상기scopus
Issue Date
2007
Journal Title
Journal of Organic Chemistry
ISSN
0022-3263JCR Link
Citation
vol. 72, no. 19, pp. 7443 - 7446
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
(Chemical Equation Presented) Ir-catalyzed allylic aminations of (E)-4-benzyloxy-2-butenyl methyl carbonate with benzylamine using Feringa's (Sa,Sc,Sc)- phosphoramidite as a chiral ligand afforded linear-aminated achiral product N,O-dibenzyl-4-amino-2-buten-1-ol regioselectively (linear/branched = >99/1), whereas the (E)-5-benzyloxy-2- pentenyl methyl carbonate showed completely opposite regioselectivity (linear/branched = >1/99) and afforded the optically active (3R)-N,O-dibenzylated 3-amino-1-penten-5-ol with very high enantioselectivity (96% ee), which was used as a key intermediate for the effective synthesis of various cyclic β-amino alcohol derivatives through ring-closing metathesis in high yields. © 2007 American Chemical Society.
DOI
10.1021/jo070998h
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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