Chiral blocks for the synthesis of cyclopentanoids from [2 + 2]-cycloadduct of dichloroketene and dimethylfulvene View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2012-03

AUTHORS

N. A. Ivanova, N. P. Akhmetdinova, Z. R. Valiullina, V. A. Akhmet’yanova, O. V. Shitikova, A. N. Lobov, K. Yu. Suponitskii, L. V. Spirikhin, M. S. Miftakhov

ABSTRACT

Opening of the α,α-dichlorocyclobutanone ring in the [2 + 2]-cycloadduct of dichloroketene and dimethylfulvene with (+)-α-methylbenzylamine gave diastereoisomeric 2-dichloromethyl-5-isopropylidene-N-(α-methylbenzyl)cyclopent-3-ene-1-carboxamides, and hydrolysis of the latter at the dichloromethyl group afforded the corresponding bicyclic aminals which can be readily separated by chromatography on silica gel. The subsequent removal of the α-methylbenzylamine fragment via reduction and hydrolysis resulted in the formation of enantiomerically pure (-)- and (+)-6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]-furan-1-ones. More... »

PAGES

442-450

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428012030190

DOI

http://dx.doi.org/10.1134/s1070428012030190

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1031262381


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