Enantioselective synthesis of α-amino acetals (aldehydes) via nucleophilic 1,2-addition to chiral 1,3-oxazolidines

A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines 4 is described. Chemical yields and diastereoselectivities are generally excellent (91–100% de). The resulting amino alcohols 6 may be oxidati...

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 41; pp. 7489 - 7492
Main Authors Muralidharan, K.Raman, Mokhallalati, Mohamed K., Pridgen, Lendon N.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.10.1994
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACIDS
PHENETHYLAMINES
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Summary:A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines 4 is described. Chemical yields and diastereoselectivities are generally excellent (91–100% de). The resulting amino alcohols 6 may be oxidatively or reductively cleaved to enantiomerically enriched α-amino acetals 3 which are useful chiral building blocks. Treatment of the oxazolidines 1 with Grignard reagents afforded the aminoalcohols 2 in good yields and high stereoselectivity.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)78325-0