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Zinc Hydroxide‐Catalyzed Asymmetric Allylation of Acetophenones with Amido‐Functionalized Allylboronate in Water
Author(s) -
Sengoku Tetsuya,
Maegawa Ryunosuke,
Imamura Hiroki,
Wada Mitsuo,
Yoda Hidemi
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000195
Subject(s) - chemistry , enantioselective synthesis , acetophenone , reagent , catalysis , zinc , diethylzinc , substituent , organic chemistry , substrate (aquarium) , hydroxide , yield (engineering) , enantiomeric excess , oceanography , materials science , geology , metallurgy
Enantioselective allylation of aldehydes and ketones is a widely used approach for preparing chiral homoallylic alcohols, however, most of the reactions are still mainly performed in organic solvents. Considering their environmental impact, expansion of synthetic technology in water has the highest priority in the organic chemistry field. Here, we report enantioselective reaction of water‐stable amido‐functionalized allylboronates with acetophenone derivatives in water. The reaction was catalyzed with zinc hydroxide and a didecylamino‐functionalized chiral aminophenol reagent, affording a variety of homoallylic alcohols in up to 99% yield. There is a definite proportional correlation between the enantioselectivity and the size of an ortho ‐substituent on the substrate, and the enantiomeric excess of the product reached up to 98%.