Simple asymmetric synthesis of optically active 3-oxabicyclo- [3.1.0]-hex-2-one derivatives

Abstract

Seven optically active 3-oxabicyclo-[3.1.0]-hex-2-one derivatives (or bicyclic lactones) were prepared from unsaturated esters of diazoacetic acid by the asymmetric intramolecular carbon addition under the action of a chiral copper catalyst, (S)-7644. The merit of this method is its simple operation using commercially available reagents. The structure of the products obtained were confirmed by elemental analysis, IR, NMR and the specific rotation, the e. e. values were also determined.

Key words: UNSATURATED ESTERS, ELEMENTAL ANALYSIS, ADDITION REACTION, BICYCLIC COMPOUND, CYCLIZATION, KETONE, NMR SPECTROMETRY, NITROGEN HETEROCYCLICS, INFRARED SPECTROPHOTOMETRY

CLC Number:

O627

Cite this article

SHI HAIJIAN;WEI QI;WU HUIJUN. Simple asymmetric synthesis of optically active 3-oxabicyclo- [3.1.0]-hex-2-one derivatives[J]. Chin. J. Org. Chem., 1997, 17(1): 76-81.

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手性3-氧杂双环[3.1.0]-己-2-酮类化合物的不对称合成