Stereocontrolled preparation of 1,2-diol with quaternary chiral center

Development of an enantio- and stereoselective construction of 1,2-diols including a quaternary chiral center was achieved by a titanium-mediated aldol reaction of lactates bearing chiral oxazolidine-2-ones. anti-Aldol and syn-aldol were selectively obtained by the choice of a benzyl and TBS protect...

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Published inTetrahedron letters Vol. 43; no. 45; pp. 8121 - 8123
Main Authors Murata, Yoshihisa, Kamino, Tomoyuki, Hosokawa, Seijiro, Kobayashi, Susumu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.11.2002
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OLEFINS
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Summary:Development of an enantio- and stereoselective construction of 1,2-diols including a quaternary chiral center was achieved by a titanium-mediated aldol reaction of lactates bearing chiral oxazolidine-2-ones. anti-Aldol and syn-aldol were selectively obtained by the choice of a benzyl and TBS protecting group, respectively. Plausible transition states are also shown based on the stereochemistry of the enolate anion. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01946-9