Reversed diastereoselectivity in the Yang photocyclization upon introducing a cyclopropyl group at the alpha position to carbonyls

Dong Jo Chang, Keepyung Nahm, Bong Ser Park

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

1-Benzoy1-1-(o-ethylphenyl)cyclopropane favors the E-indanol formation in its photochemical reaction and the selectivity is maximized in methanol. These are exactly opposite to the photochemical behavior of α-(ortho-ethylphenyl)-acetophenone. Our computational studies suggest that the different stereochemical outcome of the two systems originates from the geometric difference of initially formed biradical intermediates.

Original languageEnglish
Pages (from-to)4249-4252
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number23
DOIs
StatePublished - 3 Jun 2002

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