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[(BINAP)Re(O)Cl-3] as an efficient catalyst for olefination of chiral alpha-substituted aliphatic aldehydes
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2010 (English)In: Journal of Organometallic Chemistry, ISSN 0022-328X, E-ISSN 1872-8561, Vol. 695, no 19-20, 2220-2224 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2010. Vol. 695, no 19-20, 2220-2224 p.
Keyword [en]
Alkenes, Homogenous catalysis, Rhenium, Wittig reactions
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-24647DOI: 10.1016/j.jorganchem.2010.06.008ISI: 000280847000009OAI: oai:DiVA.org:kth-24647DiVA: diva2:352420
Note
QC 20100921Available from: 2010-09-21 Created: 2010-09-21 Last updated: 2017-12-12Bibliographically approved

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