Abstract
Chiral C2-symmetric diamines have emerged as versatile auxiliaries or ligands in numerous asymmetric transformations. Chiral 2,2’-bispyrrolidine-based salan ligands were prepared and applied to the asymmetric aryl transfer to aldehydes with arylboronic acids as the source of transferable aryl groups. The corresponding diarylmethanols were obtained in high yields with moderate to good enantioselectivitives of up to 83% ee.
Highlights
Chiral diarylmethanols are important intermediates and precursors for the synthesis of pharmacologically and biologically active compounds [1-8]
We have successfully developed an efficient and practical method for the synthesis of diarylmethanols by transmetalation using the arylboronic acid in the presence of trimethylgallium [27]
We describe our efforts toward the synthesis of optically active diarylmethanols through the asymmetric aryl transfer to aldehydes under the catalysis of (R,R)-2,2’-bispyrrolidine-based salan ligands
Summary
Chiral diarylmethanols are important intermediates and precursors for the synthesis of pharmacologically and biologically active compounds [1-8]. We have successfully developed an efficient and practical method for the synthesis of diarylmethanols by transmetalation using the arylboronic acid in the presence of trimethylgallium [27]. These methods allow the exploitation of a broad range of substituted aryl transfer reagents since numerous arylboronic acids are commercially available, and a lot of excellent ligands were developed and applied to the asymmetric aryl transfer reaction with good results [28-41]. We describe our efforts toward the synthesis of optically active diarylmethanols through the asymmetric aryl transfer to aldehydes under the catalysis of (R,R)-2,2’-bispyrrolidine-based salan ligands
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