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2005
Diastereoselective syntheses
O 0031
Stereoselective Tandem Aldol-Tishchenko Reaction with Acylsilanes. —
of lithium enolates of benzyl trimethylsilyl ketone (I) with various aldehydes
37- 031 Treatment
(II) affords the corresponding 1,3-diol monoesters (III) having three contiguous stereogenic centers with perfect levels of stereochemical control. Reaction of enolates derived from acylsilanes (IV) under similar conditions gives the corresponding 1,3-anti-diol monoester (V) in moderate yields with perfect diastereoselectivity as a single
regioisomer, whereas the reaction with α-branched aldehydes results in a mixture of
two regioisomers (VI)/(VII). — (HONDA*, M.; IWAMOTO, R.; NOGAMI, Y.; SEGI,
M.; Chem. Lett. 34 (2005) 4, 466-467; Div. Mater. Sci., Grad. Sch. Nat. Sci. Technol.,
Kanazawa Univ., Kanazawa 920, Japan; Eng.) — F. Santoso
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