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2005
Cyclopentane derivatives
Q 0030
Intramolecular Cyclization of Ene-Imine Using Dibutylzirconocene. — Ene-imigenerated from ene-aldehydes (I) or (XII) and primary amines by treatment with
04- 077 nes,
MgSO4, are transformed into cyclopentane derivatives via intermediate azazirconacycles. Ene-imines derived from amines (II) give predominantly trans-substituted cyclopentanes (IV), except for tert-butylamine which affords exclusively cis-product
(Ve). The method is also performed with various optically active primary amines to
study the stereoselectivity of this reaction. At room temperature, the larger substituents
on the starting amines decrease the yields of trans-products, whereas cis-cyclopentanes
are formed as major products upon heating. In the case of cyclopentanes derived from
aldehyde (XII), the primarily formed mixtures of diastereomers are hydrogenated followed by benzoylation to provide benzoylaminocyclopentanes (XIV)—(XVII). —
(MAKABE, M.; SATO, Y.; MORI*, M.; J. Org. Chem. 69 (2004) 19, 6238-6243;
Grad. Sch. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan; Eng.) — Klein
2005
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