82898-93-9Relevant academic research and scientific papers
Stereoselective Synthesis of Alcohols, XI. Double Stereodifferentiation in the Addition of Crotylboronates to Aldehydes: Prelog-Djerassi Lactone
Hoffmann, Reinhard W.,Zeiss, Hans-Joachim,Ladner, Wolfgang,Tabche, Susanne
, p. 2357 - 2370 (2007/10/02)
Addition of the (Z)-crotylboronate 11 to (S)-(+)-α-methylbutyraldehyde (4) resulted in the Cram and Anti-Cram diastereomers 6 and 7.Their ratio depended on the chirality of the boronate component.Hence the formation of the alcohol 7 could be favoured by double stereodifferentiation.Similarly, on addition of the (E)-crotylboronate 12 predominant formation of the isomer 13 could be achieved.These observations formed the basis for a stereoselective synthesis of the Prelog-Djerassi lactone 3.
