Practical enantioselective synthesis of β-lactones catalyzed by aluminum bissulfonamide complexes

Advanced Synthesis and Catalysis

Volumn 349, Issue 10, 2007, Pages 1647-1652

  Kull, Thomas ^a   Peters, René ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

lactones; Aluminum; Catalysis; Cycloaddition; Ketenes; Sulfonamides

Indexed keywords

EID: 34547180823     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700084     Document Type: Article

References (38)

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30. Attempts with acetyl chloride instead failed. This might be ascribed to a blocking of the hard Al ion by coordination of the hard chloride anion which is generated during the ketene formation. The coordination of the softer bromide anion is anticipated to be more labile.
31. 2AlF, -78°C, ee = 28 %, very slow reaction).
32. Both longer (6 h) and shorter (2 h) heating periods resulted in less enantioselective reactions.
33. 3 the signals for free ligand were already disappeared after 30 min.
34. Similarly, DiPh-Trip 7b/Dibal gave the following results with (a) cyclohexanecarbaldehyde 4b (0.25 M, toluene, -85°C, 45 h): 10 mol% 7b/10 mol% Dibal: 70% yield, 70% ee; 10 mol% 7b/15 mol% Dibal: 75% yield, 75% ee; (b) dihydrocinnamaldehyde 4a (0.25 M, toluene, -85°C, 44 h): 10 mol% 7b/10 mol% Dibal: 42% yield, 74% ee; 10 mol% 7b/15 mol% Dibal: 79% yield, 78% ee.
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37. Similar to previous catalytic asymmetric [2 + 2] cycloadditions of the parent ketene and aldehydes, the catalyst systems reported herein are not applicable to benzaldehyde and α,β-unsaturated aldehydes, since the products decomposed during the isolation/purification procedures presumably due to elimination reactions. The same problem was faced with conjugated ynals.
38. No clear picture is evident with regard to the reaction times: while in some cases, the conversion is complete after one day even with sterically hindered aldehydes such as cyclohexanecarbaldehyde 4b or isovaleraldehyde 4f, for other substrates up to 6 days at -85°C are necessary to achieve full conversion.