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Synlett 1997; 1997(4): 353-354
DOI: 10.1055/s-1997-804
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Zinc-Mediated Allylation of N-Protected α-Amino Aldehydes in Aqueous Solution. Stereoselective Synthesis of Anti- and Syn-β-Amino Alcohols with Functionalized Allyl Groups

Stephen Hanessian* , Haeil Park, Rui-Yang Yang
  • *Department of Chemistry, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montréal, Québec, H3C 3J7, CANADA, Fax: (514) 343-5728; e-mail hanessia@ere.umontreal.ca
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Publication History

Publication Date:
31 December 2000 (online)

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Anti-β-amino alcohols with differently substituted allyl groups were obtained in high chemical yields and in good to excellent diastereoselectivities via Zn-mediated allylation of 2-(dibenzylamino)aldehydes in aqueous media. Swern oxidation, and reduction with NaBH4 gave enantiopure syn-β-amino alcohols in good yields.

Zn-mediated allylation - α-amino aldehydes - anti-β-amino alcohols

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