A multicomponent approach for the preparation of homoallylic alcohols.

A multicomponent approach for the preparation of homoallylic alcohols† †Raw spectra can be found at DOI: 10.17863/CAM.591 ‡ ‡Electronic supplementary information (ESI) available. CCDC 1483699. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc02581a Click here for additional data file. Click here for additional data file.

One-pot enantioselective synthesis of optically active homoallylic alcohols from allyl halides.

A one-pot, convenient method for the preparation of optically active homoallylic alcohols from allyl halides was developed. Allyltrichlorosilanes were generated in situ from allyl halides and trichlorosilane in the presence of cuprous chloride and tertiary amine. Without isolation of the allyltrichlorosilanes, benzaldehyde and chiral biquinoline N,N'-dioxide were introduced into the same flask,...

Application of the lithiation-borylation reaction to the preparation of enantioenriched allylic boron reagents and subsequent in situ conversion into 1,2,4-trisubstituted homoallylic alcohols with complete control over all elements of stereochemistry.

The reactions of Hoppe's lithiated carbamates with vinylboranes and boronic esters give allylic boranes/boronic esters, and subsequent addition of aldehydes provides a new route to enantioenriched homoallylic alcohols with high enantiomeric ratios and diastereomeric ratios. Specifically, reactions of sparteine-complexed lithiated carbamates with trans-alkenyl-9-BBN derivatives followed by addit...

General and practical approach to the syntheses of linear homoallylic alcohols*

We have demonstrated that metal-mediated allylation of aldehydes can afford γ-homoallylic alcohols or α-linear homoallylic alcohols by judicious choice of the solvents. A new mechanism has been proposed to account for this new α-selective metal-mediated allylation reaction. On the other hand, the metal-mediated prenylation under the same conditions to obtain α-prenyl alcohols was unsuccessful. ...

Asymmetric 5-endo chloroetherification of homoallylic alcohols toward the synthesis of chiral β-chlorotetrahydrofurans.

An asymmetric 5-endo chloroetherification of homoallylic alcohols is successfully developed that employs an easily available quaternary ammonium salt derived from cinchonine as a conventional organocatalyst. This approach provides ready access to β-chlorotetrahydrofurans in high enantioselectivities.