ChemInform Abstract: Boron—Zinc Exchange in the Diastereoselective Arylation of Sugar‐Based Aldehydes: Stereoselective Synthesis of (+)‐7‐epi‐Goniofufurone and Analogues

Abstract

Boron-Zinc Exchange in the Diastereoselective Arylation of Sugar-Based Aldehydes: Stereoselective Synthesis of (+)-7-epi-Goniofufurone and Analogues -[81 refs.]. -(WOUTERS, A. D.; BESSA, A. B.; SACHINI, M.; WESSJOHANN, L. A.; LUEDTKE*, D. S.; Synthesis 45 (2013) 16, 2222-2233, http://dx.

The inexpensive additive N‐methylmorpholine effectively decreases the equivalents of nucleophiles in the catalytic highly enantioselective arylation of aryl aldehydes

“…And the loading of nucleophilic triarylaluminums in the catalytic enantioselective arylation of aldehydes is first reduced to the equimolar to aldehydes, greatly increasing the practicability of the process. Experiments on solvents finally confirmed that mixed THF/hexane was the preferred solvent (entries [15][16][17]. Therefore, the optimal reaction conditions were determined (entry 13).…”

“…[1][2][3][4][5][6][7][8] Accordingly, the catalytic asymmetric addition of arylmetal reagents and aryl boronic acids to aldehydes has attracted considerable attention over the past decades. [9][10][11][12][13][14][15][16][17] Since Fu and coworkers seminally reported the asymmetric addition with Ph 2 Zn, 18 arylzinc reagents from various aryl sources such as arylboronic acids have been commonly explored for the enantioselective synthesis of diarylmethanols. [19][20][21][22][23][24][25][26][27][28][29][30] Meanwhile, other active aryl metals such as arylaluminum, arylmagnesium, and aryllithium have transferred aryl to less active aryl titanium intermediates ArTi(Oi-Pr) 3 as nucleophiles for enantiopure diarylmethanols because of their higher reactivity.…”

“…Enantiopure diarylmethanols are important structural scaffolds in the synthesis of pharmaceuticals and bioactive compounds . Accordingly, the catalytic asymmetric addition of arylmetal reagents and aryl boronic acids to aldehydes has attracted considerable attention over the past decades . Since Fu and coworkers seminally reported the asymmetric addition with Ph 2 Zn, arylzinc reagents from various aryl sources such as arylboronic acids have been commonly explored for the enantioselective synthesis of diarylmethanols .…”