ChemInform Abstract: Chiral Blocks for the Synthesis of Cyclopentanoids from [2 + 2]‐Cycloadduct (I) of Dichloroketene and Dimethylfulvene.

Abstract

Dimethylfulvene. -The opening of the cyclobutanone ring in compound (I) proceeds readily under the action of chiral amine (II) to afford inseparable diastereomeric amides (III) and (IV), which are converted into separable lactams (V) and (VI). The reduction of individual lactams followed by acidic hydrolysis of hydroxymethyl amides leads to the desired enantiopure lactones [cf. (VIII)]. -(IVANOVA, N. A.; AKHMETDINOVA, N. P.; VALIULLINA, Z. R.; AKHMET'YANOVA, V. A.; SHITIKOVA, O. V.; LOBOV, A. N.; SUPONITSKII, K. Y.; SPIRIKHIN, L. V.; MIFTAKHOV, M. S.; Russ. J. Org. Chem. 48 (2012) 3, 442-450, http://dx.