Diastereoselective Oxidative Coupling of Enolates of 3-Phenylpropionic Acid Derivatives - EPC Synthesis of ent-Hinokinin

Synlett

Volumn 1996, Issue 11, 1996, Pages 1137-1139

  Langer, Thomas ^a   Illich, Michael ^a   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007165385     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5668     Document Type: Article

References (24)

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11. 2 in 3 ml of THF. After 15 min work-up was carried out as described above. Purification of the crude product by MPLC (silica gel, petroleum ether/ethyl acetate 8:2, flow: 30 ml/min, UV detection) yielded 35 % of 7a as colorless needles (mp. 102-103 °C) and 51 % of 7b as colorless needles (mp. 128-129 °C).
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13. 4Cl solution was added and the mixture worked up as usual. Products were purified by flash chromatography on silica gel with petroleum ether/ethyl acetate mixtures as eluents.
14. While the absolute configuration of (S,S)-3 could be determined by saponification to the corresponding known diacid (B. Cammalm, Chem. Ind. 1956, 1093), absolute configurations of (S,S)-6 and (S,S)-9 have not yet been determined as the absolute configurations of the corresponding diacids are unkown.
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23. The compound (R,R)-12 was formed only in small amounts and could not be isolated. It was identified by its UV spectra (diode array detector) which were superposable to those of (S,S)-12.
24. 9e.