Kinetic Resolution of 1, 1′‐Biaryl‐2, 2′‐Diols and Amino Alcohols through NHC‐Catalyzed Atroposelective Acylation
S Lu, SB Poh, Y Zhao - Angewandte Chemie International …, 2014 - Wiley Online Library
S Lu, SB Poh, Y Zhao
Angewandte Chemie International Edition, 2014•Wiley Online LibraryWe present here a highly efficient NHC‐catalyzed kinetic resolution of a wide range of 1, 1′‐
biaryl‐2, 2′‐diols and amino alcohols to provide them in uniformly≥ 99% ee. This
represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The
aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found
to have a significant effect on the enantioselectivity of the process.
biaryl‐2, 2′‐diols and amino alcohols to provide them in uniformly≥ 99% ee. This
represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The
aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found
to have a significant effect on the enantioselectivity of the process.
Abstract
We present here a highly efficient NHC‐catalyzed kinetic resolution of a wide range of 1,1′‐biaryl‐2,2′‐diols and amino alcohols to provide them in uniformly ≥99 % ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.
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