The triisopropylsilyl effect: Exceptional Cram-type selectivity in Mukaiyama aldol reactions of a silyl ketene thioacetal

Chemical Communications

Volumn , Issue 17, 1998, Pages 1797-1798

  Davis, Anthony P ^a   Plunkett, Stephen J ^a   Muir, Jayne E ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

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EID: 0011229770     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804153i     Document Type: Article

References (24)

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21. For comparison, additions to 4 usually result in ca. 1:1 ratios of diastereomers (recent example: J. J. Eshelby, P. J. Parsons and P. J. Crowley, J. Chem. Soc., Perkin Trans, 1, 1996, 191).
22. Even a highly hindered lithium α,α:-bis(alkylthio) enolate gave a ratio of just 3.5:1 with this substrate [ref. 3(c)]. Only the arylthionation-allylation of Heathcock, which is not a simple addition reaction, gives selectivities comparable with the present method (I. Mori, P. A. Bartlett and C. H. Heathcock, J. Am. Chem. Soc., 1987, 109, 7199).
23. Macromodel V5.5, MM3*force field. See; F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440.
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