Olefination of α-Hydroxy or α-Aminoaldehyde Derivatives via Reaction of Their Arylsulfonylhydrazones with Sulfonyl Anions
摘要:
Reaction of tosylhydrazones of O-substituted a-hydroxy or N-substituted a-amino aldehydes (2, 7, 11, 15, 17, and 20) with selected alpha-magnesio alkyl phenyl sulfones afforded the respective derivatives of allylic alcohols or allylic amines. 2,3-O-Isopropylidene-D-glyceraldehyde (1) was transformed into its tosylhydrazone (2) and then olefins 4a with retention of optical purity.
A Chiral Sulfoxide-Ligated Ruthenium Complex for Asymmetric Catalysis: Enantio- and Regioselective Allylic Substitution
作者:Barry M. Trost、Meera Rao、André P. Dieskau
DOI:10.1021/ja411310w
日期:2013.12.11
and synthesis of a novel chiral sulfoxide-ligated cyclopentadienyl ruthenium complex is described. Its utility as an asymmetric variant of [CpRu(MeCN)3]PF6 is demonstrated through its ability to function in the branched-selective asymmetric allylic alkylation of phenols and carboxylic acids. Water has also been shown to act as a competent nucleophile in this reaction to generate branched allyl alcohols