On 1,4-diastereoselectivity in the chiral allylsilane addition to chiral α-substituted aldehydes

Tetrahedron Letters

Volumn 39, Issue 30, 1998, Pages 5343-5346

  Dias, Luiz C ^a   Giacomini, Rosana ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE;

ARTICLE; CHELATION; CHIRALITY; CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032560775     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01066-1     Document Type: Article

References (17)

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6. (c)We use the "Felkin" descriptor to refer to the diastereomer predicted by the Felkin-Ahn paradigm. The "anti-Felkin" descriptor refers to diastereomers not predicted by this transition state model.
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11. (b) Mickelson, T.J.; Koviach, J.L.; Forsyth, C.J. J. Org. Chem. 1996, 61, 9617-9620.
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14. 9.Standard literature methods were employed. The final step in each case was Swern oxidation of the corresponding alcohol. Attempts to purify aldehydes 3-6 by silica-gel chromatography resulted in partial racemization. Since the diastereoselectivity of the reactions of these aldehydes with allylsilane 2 depends on their enantiomeric purity, crude aldehydes were used in all of the studies described in the text. It should be noted that partial racemization probably is occurring during reaction since we observed small peaks at δ 1.0-1.2 ppm.
15. 10.(a) Schreiber, S.L.; Shambayati, S.; Blake, J.F.; Wierschke, S.G.; Jorgensen, W.L. J. Am. Chem. Soc. 1990, 112, 697-703,
16. 13 C-NMR, IR, MS, and HRMS spectral data.
17. 4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (30% EtOAc/hexanes) afforded the corresponding homoallylic alcohols.