141550-15-4Relevant academic research and scientific papers
Stereospecific Pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides
Li, Ling,Zhao, Shibin,Joshi-Pangu, Amruta,Diane, Mohamed,Biscoe, Mark R.
, p. 14027 - 14030 (2015/01/08)
We report the development of a Pd-catalyzed process for the stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo cross-coupling reactions with stereospecific inversion of configuration using this method.
Highly (E)-selective BF3·Et2O-promoted allylboration of chiral nonracemic α-Substituted allylboronates and analysis of the origin of stereocontrol
Chen, Ming,Roush, William R.
scheme or table, p. 2706 - 2709 (2010/11/18)
(Figure presented) δ-Methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z >30:1 and 93% to >95% ee via BF 3·Et2O-promoted allylboration with α-Me-allylboronate 1. The origin of high (E)-selectivity is proposed
Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of β-substituted α-amino acid derivatives
O'Donnell, Martin J.,Cooper, Jeremy T.,Mader, Mary M.
, p. 2370 - 2371 (2007/10/03)
Optically active syn- or anti-β-substituted-α-amino acid derivatives are prepared in 94 to ≥99% ee and 66-98% ds by reaction of the Schiff base acetate of glycine tert-butyl ester with chiral, nonracemic B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine (CdOH) or cinchonine (CnOH), base, and lithium chloride. Copyright
