4798-60-1Relevant articles and documents
Highly diastereoselective and enantiospecific allylation of ketones and imines using borinic esters: Contiguous quaternary stereogenic centers
Chen, Jack L.-Y.,Aggarwal, Varinder K.
supporting information, p. 10992 - 10996 (2015/03/30)
3,3-Disubstituted allylic boronic esters are not sufficiently reactive to react with ketones and imines. However they can be converted into the corresponding borinic esters by the sequential addition of nBuLi and TFAA. These reactive intermediates possess
Modulating the stereochemical outcome of the Ireland-Claisen reaction of (E)- and (Z)-allylic glycolates
Feldman, Ken S.,Selfridge, Brandon R.
supporting information; experimental part, p. 825 - 828 (2012/03/09)
The diastereoselectivity of Ireland-Claisen rearrangements of allylic glycolates is dependent on the E:Z ratio of the silyl ketene acetals, the alkene geometry in the allyl unit, and the transition state topography. High yields and excellent diastereoselectivities (>95:5) have been achieved for selected substrates, including those with R2 = ethyl that results in a newly formed quaternary center. A discussion of the scope, selectivities, and transition state models will be presented.
An optimised and recoverable tartrate surrogate for sharpless asymmetric epoxidations
Knight, David W.,Morgan, Ian R.
scheme or table, p. 35 - 38 (2009/05/07)
The tetrahydroxy diester 7d (R = iPr) is almost as effective as diisopropyl tartrate in SAE reactions of (E)-allylic alcohols and can be recovered and re-used following a relatively simple work-up procedure.
