The "benzostabase" protecting group for primary amines; application to aliphatic amines

Article abstract of DOI:10.1016/S0040-4039(00)97158-2

The "benzostabase" (BSB) protecting group has been applied to primary aliphatic amines. It can be introduced via a dehydrogenative silylation employing an air- and moisture-stable reagent, and is appreciably more acid-stable than the related "stabase" group. BSB protection has been used in a stereoselective synthesis of amino-alcohols involving the addition of organometallic reagents to protected amino-aldehydes under "non-chelation control".