Resolution of trans-2-azidocycloalkanols by separation of their mandelic acid esters
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Tarih
2023
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Pergamon-Elsevier Science Ltd
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
It is presented that resolution of (+/-)-trans-2-azidocylohexanol and (+/-)-trans-2-azidocyclooctanol can be effected with (R)-mandelic acid. (R)-Mandelate esters of these azido alcohols can be separated by column chromatog-raphy on silica gel in an efficient manner. Upon methanolysis (transesterification) of the diastereomerically pure (R)-mandelate esters by K2CO3, enantiomerically pure trans-2-azidocylohexanols and trans-2-azidocyclooctanols are obtained. Their synthetic relevance has been also demonstrated by subjecting them to some enantiospecific transformations, such as the Mitsunobu reaction and hydrogenolysis of the azide functionality. Notably, this is the first study reporting the preparation of enantiopure trans-2-azidocyclooctanols.
Açıklama
Anahtar Kelimeler
Azides, Azido alcohols, Chiral resolution, Resolution with mandelic acid, Resolution oftrans-2-azidocycloalkanols, Asymmetric synthesis
Kaynak
Tetrahedron Letters
WoS Q Değeri
Q3
Scopus Q Değeri
Q3
Cilt
133
