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[(BINAP)Re(O)Cl-3] as an efficient catalyst for olefination of chiral alpha-substituted aliphatic aldehydes

Författare

Summary, in English

A convenient one-pot preparation of [(BINAP) Re(O)Cl-3] (6) is described. This complex was demonstrated to be an efficient catalyst for the olefination of aldehydes by reaction with alpha-diazo esters, with essentially quantitative yields and up to 98:2 geometric selectivity. The potential for using enantiopure [(BINAP)Re(O)Cl-3] (6) to promote an asymmetric kinetic resolution of racemic alpha-stereogenic aldehydes was investigated, but no enantiotopic discrimination was observed. Control experiments indicate that this lack of selectivity stems from the in-situ formation of a phosphonium ylide, which accounts for product formation in a non-metal associated reaction pathway. (C) 2010 Elsevier B. V. All rights reserved.

Publiceringsår

2010

Språk

Engelska

Sidor

2220-2224

Publikation/Tidskrift/Serie

Journal of Organometallic Chemistry

Volym

695

Issue

19-20

Dokumenttyp

Artikel i tidskrift

Förlag

Elsevier

Ämne

  • Organic Chemistry

Nyckelord

  • Rhenium
  • Alkenes
  • Homogenous catalysis
  • Wittig reactions

Status

Published

ISBN/ISSN/Övrigt

  • ISSN: 0022-328X