Stereoselectivity of the annelation of 3,4-dihydroisoquinolines by 5-monosubstituted 2-acylcyclohexane-1,3-diones

The annelation of 1-methyl-3,4-dihydroisoquinoline by prochiral 5-substituted 2-acylcyclohexane-1,3-diones proceeds diastereoselectively yielding a 9 R,16 R:9 S,16 S pair of enantiomers rather than a possible mixture of four 8-aza-D-homogona-12,17 a-dione stereoisomers; this stereoselectivity result...

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Published inMendeleev communications Vol. 9; no. 3; pp. 119 - 121
Main Authors Gulyakevich, Olga V., Rubinova, Irene L., Rubinov, Dmitry B., Govorova, Alla A., Lyakhov, Alexander S., Mikhal’chuk, Alexander L.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 1999
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Summary:The annelation of 1-methyl-3,4-dihydroisoquinoline by prochiral 5-substituted 2-acylcyclohexane-1,3-diones proceeds diastereoselectively yielding a 9 R,16 R:9 S,16 S pair of enantiomers rather than a possible mixture of four 8-aza-D-homogona-12,17 a-dione stereoisomers; this stereoselectivity results from the impossibility of a threo-attack on the prochiral β,β’-triketone by azomethyne owing to the spatial structure of 2-acylcyclohexane-1,3-dione, on the one hand, and by the steric effect of the C(1) methyl group of 3,4-dihydroisoquinoline, on the other.
ISSN:0959-9436
DOI:10.1070/MC1999v009n03ABEH001065