Chiral sulfoxide ligands in catalytic asymmetric cyanohydrin synthesis

Synlett

Volumn , Issue 2, 2003, Pages 236-240

  Rowlands, Gareth J ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

Aldehydes; Catalysis; Chiral sulfoxides; Cyanohydrins

Indexed keywords

ALDEHYDE DERIVATIVE; CYANOHYDRIN; LIGAND; SULFOXIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037281833     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-36790     Document Type: Article

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70. 4) and concentrated. The cyanohydrin 9 was isolated by column chromatography (petroleum ether:ether, 3:1).
71. 4 + 10% DMSO over the same period. Again this indicates that the ligand is essential for activity. The decrease in the rate of reaction in the presence of DMSO could possibly be the result of the formation of a coordinatively saturated octahedral complex with resultant loss in Lewis acidity. This would require two equivalents of DMSO per titanium centre thus resulting in only 5% active catalyst being present. Stoichiometry of the catalyst has already been shown to effect the rate (Table 1; entry 6).
72. Three aluminium complexes were studied in cyanosilylation reaction of benzaldehyde. One formed from 2,2′-biphenol gave 58% conversion, one with a phenyl sulfone substituent in the ortho position of 2,2′-biphenol gave 75% conversion whilst the phenyl sulfoxide substituted 2,2′-biphenol gave 92% conversion. This suggests that the sulfoxide is activating the TMSCN and that it is not purely an electronic effect making the aluminium centre more Lewis acidic. Work to convert this to a chiral system is currently underway.
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