Conformational Diagnosis of Diethyl (4S,5S)-4,5-Bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate Based on the Stereochemical Outcomes of Representative Reactions As Compared with Those of Its 4,5-O-Isopropylidene Derivatives and on a Dichroic Exciton Chirality Method

Seiki Saito, Osamu Narahara, Teruhiko Ishikawa, Masahiro Asahara, Toshio Moriwake, Jacek Gawronski, Franciszek Kazmierczak

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45 Citations (Scopus)

Abstract

In order to gain more insight into the conformation of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate (1) experimentally, some appropriate reactions of 1 and its derivative (S,S)-3, which bears isopropylidene protecting groups, have been executed. The stereochemical outcomes of such reactions as the Diels-Alder reaction, osmium tetraoxide-catalyzed hydroxylation, conjugate addition with amines, and cyclopropanation with phosphonium ylides point to a rigid conformation (1A) in which the vicinal TBDMSO groups, the most bulky substituents, are arranged in an anti relationship, and, therefore, the enoate groups are forced to be gauche each other. A dichroic exciton chirality study has also provided clear-cut evidence for this rigid conformation.

Original languageEnglish
Pages (from-to)6292-6302
Number of pages11
JournalJournal of Organic Chemistry
Volume58
Issue number23
DOIs
Publication statusPublished - 1993

ASJC Scopus subject areas

  • Organic Chemistry

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