Study on the reaction mechanism of Heck-oxyarylation of 2H-chromenes

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The Heck-oxyarylation reaction of deuterium labeled 2H-chromenes (12,15) has been studied whose synthesis was achieved in four steps starting from the readily available 7- benzyloxychromane (9). Since the deuterium label was not affected in the course of the oxyarylation, the formation of the neutral achiral intermediate 7 could be ruled out as a possible reaction pathway and a reason for the lack of enantioselectivity in asymmetric Heckoxyarylations. This also allowed the simple synthesis of 6a- and 11a-deutero-3- benzyloxypterocarpanes (13a,b).

Original languageEnglish
Pages (from-to)103-110
Number of pages8
JournalArkivoc
Volume2009
Issue number6
DOIs
Publication statusPublished - 2009

    Fingerprint

Keywords

  • Heck-oxyarylation
  • Mechanism
  • Pterocarpan

ASJC Scopus subject areas

  • Organic Chemistry

Cite this