Model study for steroidal D/C ring closure in olefinic cyclization reactions; a MINDO/3 study

A. Corvers, P.C.H. Scheers, W.A.M. Castenmiller, H.M. Buck

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

5 Citaten (Scopus)

Samenvatting

MINDO/3 molecular orbital calculations are performed for the ring closure of (Z)- and (E)-allkenes as a model for the D/C ring closure to steroids. It is shown that a lower activation energy is needed for cyclizations in the chair configuration, than for cyclizations in the boat configuration. An analogous picture is found by comparison of (E)- and (Z)-alkenes. Cyclization of the (E)-alkene in the chair or boat configuration is energetically favoured over the ring closure of (Z)-alkenes. These results are in agreement with the Stork-Eschenmoser hypothesis.
Originele taal-2Engels
Pagina's (van-tot)457-459
Aantal pagina's3
TijdschriftTetrahedron
Volume34
Nummer van het tijdschrift4
DOI's
StatusGepubliceerd - 1978

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