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Synlett 2000; 2000(1): 37-40
DOI: 10.1055/s-2000-6461
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Chiral Allylsilane Additions to Chiral N-Boc-α-Amino Aldehydes

Luiz C. Dias* , Paulo R. R. Meira
  • *Instituto de Quimica, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, CEP: 13083-970, Campinas, SP, Brazil; Fax (019)-788-3023; E-mail: ldias@iqm.unicamp.br
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Publication Date:
31 December 2000 (online)

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Addition of chiral allylsilane 4 to chiral N-Boc-α-amino aldehydes in the presence of SnCl4 in CH2Cl2 at -78 °C affords 1,2-syn homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The diastereoselectivity depends on the aldehyde absolute configuration, with (R)-α-aminoaldehydes (matched case/anti-Felkin addition) exhibiting higher stereoselectivity than its enantiomer (mismatched case/Felkin addition).

chiral allylsilane - α-amino aldehydes - dipeptide isosteres - homoallylic alcohols - oxazolidines