Stereoselective construction of optically active bicyclo[3.3.0]octenone derivatives based on the Pauson–Khand reaction
- 1 January 1998
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 17,p. 2903-2916
- https://doi.org/10.1039/a803072c
Abstract
A new procedure for synthesis of optically active bicyclo[3.3.0]octenone derivatives possessing two distinguishable hydroxy groups was developed based on the intramolecular Pauson–Khand reaction of optically active enynes, which were easily prepared from dimethyl L-tartrate. (4S,5S)-4,5-Bis(tert-butyldimethylsiloxy)-7-(trimethylsilyl)hept-1-en-6-yne, for example, afforded (5S,7S,8S)-7,8-bis(tert-butyldimethylsiloxy)-2-(trimethylsilyl)bicyclo[3.3.0]oct-1-en-3-one exclusively, whereas (3S,4S)-3,4-dihydroxy-7-(trimethylsilyl)hept-1-en-6-yne produced (5R,6S,7S)-6,7-dihydroxy-2-(trimethylsilyl)bicyclo[3.3.0]oct-1-en-3-one in a highly stereoselective manner.Keywords
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