DIASTEREOSELECTIVITY ENHANCEMENT IN VINYLCUPRATE ADDITION TO BETA-ALKOXYALDEHYDES VIA A VINYLSILANE

The presence of a removable 1-(trimethylsilyl) residue greatly increases the chelation-controlled diastereoselectivity in alkenylcuprate additions to chiral beta-alkoxyaldehydes. Several methods for protiodesilylation of the resultant allylic alcohols [5 --> 2b (R = Me3SiCH2CH2OCH2-, PhCH2OCH2-,...

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Bibliographic Details
Published inTetrahedron letters Vol. 32; no. 7; pp. 857 - 858
Main Authors BURKE, SD, PISCOPIO, AD, MARRON, BE, MATULENKO, MA, PAN, G
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 11.02.1991
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONTROLLED NUCLEOPHILIC ADDITIONS
ALPHA
HIGHLY EFFECTIVE SYSTEM
ORGANOMETALLICS
ASYMMETRIC INDUCTION
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Summary:The presence of a removable 1-(trimethylsilyl) residue greatly increases the chelation-controlled diastereoselectivity in alkenylcuprate additions to chiral beta-alkoxyaldehydes. Several methods for protiodesilylation of the resultant allylic alcohols [5 --> 2b (R = Me3SiCH2CH2OCH2-, PhCH2OCH2-, and PhCH2-)T are compared.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)92104-X