33124-21-9Relevant academic research and scientific papers
Catalytic asymmetric couplings of ketenes with aldehydes to generate enol esters
Schaefer, Carsten,Fu, Gregory C.
, p. 4606 - 4608 (2007/10/03)
(Chemical Equation Presented) With a little help from the ferrocenyl catalyst ((-)-1), a wide array of α-arylalkanoic acid derivatives can be produced from the catalytic asymmetric coupling of ketenes with aldehydes (see scheme). The enol esters are readily transformed into other useful families of compounds such as carboxylic acids and alcohols.
Chiral α-substituted carbonyls and alcohols from the S(N)2' displacement of cuprates on chiral carbonates: An alternative to the alkylation of chiral enolates
Spino,Beaulieu,Lafreniere
, p. 7091 - 7097 (2007/10/03)
A highly stereoselective sequence of reactions, based on the anti-selective S(N)2' addition of cuprates to allylic carbonates, transforms alkynes or alkenyl halides into carbonyls having α-chiral centers. The method, which uses menthone as a chiral auxiliary, is a useful alternative to the alkylation of chiral enolates with the added advantage of allowing for the 'alkylation' of sec- and tert-alkyl and aryl groups.
STEREOCHEMISTRY OF THE SN2' DISPLACEMENT OF CHIRAL 1,3-DISUBSTITUTED BROMOALLENES TO FORM CHIRAL ACETYLENES
Corey, E. J.,Boaz, Neil W.
, p. 3059 - 3062 (2007/10/02)
Optically active 1,3-disubstituted bromoallenes react with a variety of cuprate reagents preferentially is an SN2' fashion with very high anti selectivity.
Stereochemistry of Aliphatic Carbocations, 15. Rearrangements in 2-Arylalkyl Systems
Kirmse, Wolfgang,Guenther, Bernd-Rainer,Loosen, Karin
, p. 2140 - 2153 (2007/10/02)
Phenyl shifts from secondary to primary carbon proceed with virtually complete inversion at the migration origin, regardless whether they are induced by solvolysis of the aryl sulfonate 25 or by deamination of the amines 12, 17, 26, and 43.Sequential rearrangements (Ph, CH3 and Ph, H) are likewise stereo- and regiospecific.These results strongly support the intervention of phenonium ions.In contrast, the competitive alkyl shifts (deamination only) from benzylic to primary carbon produce but a small excess of inversion (Me 27percent, Et 13percent, iPr 20percent, tBu 3percent).Obviously, benzyl cations are the predominant intermediates.
