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

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.

• Author: Daniel Strand; Tobias Rein
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2010
• Language: English
• Pages: 2220-2224
• Publication/Series: Journal of Organometallic Chemistry
• Volume: 695
• Issue: 19-20
• Links: http://dx.doi.org/10.1016/j.jorganchem.2010.06.008
• Document type: Journal article
• Publisher: Elsevier
• Topic: Organic Chemistry
• Keywords: Rhenium; Alkenes; Homogenous catalysis; Wittig reactions
• Status: Published
• ISBN/ISSN/Other: ISSN: 0022-328X