Novel, cyclic and bicyclic 1,3-diols as catalysts for the diethylzinc addition to aldehydes

Ian Sarvary, YQ Wan, Torbjörn Frejd

Forskningsoutput: TidskriftsbidragArtikel i vetenskaplig tidskriftPeer review

Sammanfattning

A number of optically pure 1,3-diols have been synthesized and used as catalysts in the asymmetric addition of diethylzinc to aromatic aldehydes. Enantiomeric excesses of up to 92% of (R)-1-phenylpropan-1-ol were obtained with anisylbicyclo[2.2.2] octanediol (14) as a catalyst. Using 2-picolylbicyclo[ 2.2.2] ocatanediol (16) as the catalyst resulted in a reversal of the stereoselectivity, yielding (S)-1-phenylpropan-1-ol in 83% ee. A pronounced positive non-linear effect was observed when varying the enantiomeric purity of catalyst 14.
Originalspråkengelska
Sidor (från-till)645-651
TidskriftJournal of the Chemical Society - Perkin Transactions 1
Nummer5
DOI
StatusPublished - 2002

Bibliografisk information

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Ämnesklassifikation (UKÄ)

  • Organisk kemi

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