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2005
Carbohydrates
U 0500
Mimicking Dihydroxy Acetone Phosphate-Utilizing Aldolases Through OrganoA Facile Route to Carbohydrates and Aminosugars. — The aldol reac33- 239 catalysis:
tion between various protected dihydroxy acetones and aldehydes in the presence of
(S)-proline or (S)-2-pyrrolidine-tetrazole is investigated. The cyclic substrates afford
polyol products in excellent yield and very high e.e. The diastereoselectivity depends
on the protecting group and is generally higher at 4 °C than at ambient temperature.
Aliphatic aldehydes provide higher stereoselectivity than the aromatic ones. Further
elaboration [cf. (IX)] allows the access of open-chain carbohydrate segments. —
(SURI, J. T.; RAMACHARY, D. B.; BARBAS*, C. F. I.; Org. Lett. 7 (2005) 7,
1383-1385; Dep. Chem., Scripps Res. Inst., San Diego, La Jolla, CA 92037, USA;
Eng.) — R. Steudel
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