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2004
Pyrimidine derivatives
R 0510
Anomalous Regioselective Four-Member Multicomponent Biginelli Reaction II:
Parallel Synthesis of Spiro Heterobicyclic Aliphatic Rings. — Cyclic lac46- 149 One-Pot
tams derived from glycine, alanine, or phenylalanine undergo condensation with two
molecules of aromatic aldehydes and urea to give spirodihydropyrimidines exclusively
as syn products. In the case of chiral lactams (VI) or (IX), the products are obtained
stereoselectively as mixtures of only two diastereoisomers bearing three asymmetric
carbons. The stereo/regioselectivity is driven by the nature of the substituents on the
starting lactam. — (BYK*, G.; KABHA, E.; J. Comb. Chem. 6 (2004) 4, 596-603;
Dep. Chem., Bar-Ilan Univ., Ramat Gan 52900, Israel; Eng.) — Klein
2004
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