Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters.
A new method for the Rh(I)-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters has been developed for the asymmetric synthesis of arylglycine derivatives. This method provides high yields (61-90%) and diastereoselectivities (>98:2) for a variety of functionalized arylboronic acids. The N-sulfinyl arylglycine ester products are versatile intermediates for further transformations, including selective protecting group removal, conversion to beta-amino alcohols, and direct incorporation into peptides.
Beenen
Melissa A
MA
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Weix
Daniel J
DJ
Ellman
Jonathan A
JA