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Cover Picture: Stereoselective Glycosylations Using ( R )‐ or ( S )‐(Ethoxycarbonyl)benzyl Chiral Auxiliaries at C‐2 of Glycopyranosyl Donors (Eur. J. Org. Chem. 22/2006)
Author(s) -
Kim JinHwan,
Yang Hai,
Khot Vishal,
Whitfield Dennis,
Boons GeertJan
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200690044
Subject(s) - chemistry , stereoselectivity , substituent , chirality (physics) , stereochemistry , glycosylation , ring (chemistry) , glycoside , epoxide , organic chemistry , catalysis , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Abstract The cover picture shows the proposed mechanistic pathway for the stereoselective glycosylation based on Density Functional Theory calculations of the model compound. The protected sugar that has a chiral protecting group that is derived from mandelic acid and is attached to O‐2 after activation to an oxacarbenium ion species can form energetically favorable 6‐membered‐ring dioxolenium ions. The favored dioxolenium ion has the phenyl substituent in an equatorial position in both cases, allowing for the chirality of the protecting group to be transferred to the stereochemistry of the synthetically isolated glycoside. Details are discussed in the article by D. Whitfield, G.‐J. Boons et al. on p. 5007 ff.