92215-97-9Relevant academic research and scientific papers
Copper-Catalyzed Tandem Hydrocupration and Diastereo- and Enantioselective Borylalkyl Addition to Aldehydes
Jang, Won Jun,Yun, Jaesook
, p. 12116 - 12120 (2018)
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.
Enantio- and diastereoselective synthesis of 1,2-hydroxyboronates through Cu-Catalyzed additions of alkylboronates to aldehydes
Joannou, Matthew V.,Moyer, Brandon S.,Meek, Simon J.
supporting information, p. 6176 - 6179 (2015/06/02)
The first catalytic enantio- and diastereoselective synthesis of 1,2-hydroxyboronates is reported. Reactions are promoted by a readily available chiral monodentate phosphoramidite-copper complex in the presence of an alkyl 1,1-diboron reagent. Products contain two contiguous stereogenic centers and are obtained in up to 91% yield, >98:2 d.r., and 98:2 e.r. The reaction is tolerant of aryl and vinyl aldehydes, and the 1,2-hydroxyboronate products can be transformed into versatile derivatives. Mechanistic experiments indicate control of absolute stereochemistry of the α-boryl component.
On the Steric Course of Bakers's Yeast Reduction of α-Hydroxy Ketones
Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Spreafico, Franco,Zirotti, Carlo,Casati, Paolo
, p. 4087 - 4089 (2007/10/02)
The baker's yeast mediated conversion of the α-hydroxy ketones 1-6 into the diols 8-14 is reported.
