Journal of Organic Chemistry p. 3286 - 3294 (1991)
Update date:2022-07-30
Topics:
Rangaishenvi, Milind V.
Singaram, Bakthan
Brown, Herbert C.
2-(α-Methylalkyl)- or 2-(α-arylethyl)-1,3,2-dioxaborinanes, RMeHC*BO2(CH2)3 (R = alkyl or aryl), of very high enantiomeric purity, not available from asymmetric hydroboration, can be prepared by the Matteson asymmetric homologation procedure of optically pure pinanediol or 2,3-butanediol boronate esters with (dichloromethyl)lithium, LiCHCl2, conveniently generated in situ in THF at -78 deg C, followed by reaction with either a Grignard reagent or an alkyllithium, with subsequent removal of the chiral auxiliaries. α-Methyl boronic esters thus obtained are readily converted into the corresponding aldehydes by the reaction with
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(1991)