10082-36-7Relevant articles and documents
TOTAL SYNTHESIS AND PROPERTIES OF PROSTAGLANDINS. VI. THE STEREOSPECIFICITY OF THE REDUCTION OF SOME γ-KETO ESTERS (MODELS OF PROSTAGLANDINS OF THE E SERIES) WITH SODIUM BOROHYDRIDE
Freimanis, Ya. F.,Dikovskaya, K. I.,Ignatovich, L. G.,Kudryashova, V. V.,Korits, V. R.,et al.
, p. 1282 - 1289 (2007/10/02)
The degree of stereospecificity in the reduction of cyclopentanone γ-keto esters with sodium borohydride was investigated with respect to the presence of substituents at the C2, C3, or C4 atoms of the cyclopentane ring.It was found that they have different effective directing effects on cis attack by the borohydride ion (cis in relation to the substituent at the C2 atom).It is suggested that the substituent which directs the BH4(1-) ion "to its own side" and gives rise to the degree of stereospecificity in the reduction is the alkoxycarbonyl group at the C2 atom of the cyclopentanone ring in the γ-keto esters.
