82954-89-0Relevant articles and documents
Copper-Catalyzed Tandem Hydrocupration and Diastereo- and Enantioselective Borylalkyl Addition to Aldehydes
Jang, Won Jun,Yun, Jaesook
supporting information, p. 12116 - 12120 (2018/09/11)
We report the copper-catalyzed stereoselective addition of in situ generated chiral boron-α-alkyl intermediates to various aldehydes including α,β-unsaturated aldehydes under mild conditions. This tandem and multicomponent method facilitated the synthesis of enantiomerically enriched 1,2-hydroxyboronates bearing contiguous stereocenters in good yield with high diastereo- and enantioselectivity up to a ratio greater than 98:2. In particular, α,β-unsaturated aldehydes were successfully used as electrophiles in Cu?H catalysis through 1,2-addition without significant reduction. The resulting 1,2-hydroxyboronates were used in various transformations.
Aluminum Hydride Catalyzed Hydroboration of Alkynes
Bismuto, Alessandro,Thomas, Stephen P.,Cowley, Michael J.
supporting information, p. 15356 - 15359 (2016/12/06)
An aluminum-catalyzed hydroboration of alkynes using either the commercially available aluminum hydride DIBAL-H or bench-stable Et3Al?DABCO as the catalyst and H-Bpin as both the boron reagent and stoichiometric hydride source has been developed. Mechanistic studies revealed a unique mode of reactivity in which the reaction is proposed to proceed through hydroalumination and σ-bond metathesis between the resultant alkenyl aluminum species and HBpin, which acts to drive turnover of the catalytic cycle.