American Chemical Society
ol5b01048_si_001.pdf (3.02 MB)

Stereoselective Synthesis of 1,4-Diols by a Tandem Allylboration–Allenylboration Sequence

Download (3.02 MB)
journal contribution
posted on 2015-05-01, 00:00 authored by Tony S. N. Zhao, Jian Zhao, Kálmán J. Szabó
The reaction of mono- and dialdehydes with bis-borodienes (incorporating an allylboronate unit) has been studied. It was found that the initial allylboration reaction results in an allenylboronate, which has two stereogenic units: one of them has axial chirality and the other one is a stereogenic carbon center. This reaction proceeds with high diastereoselectivity. The allenylboronate formed in the allylboration reacts with an additional aldehyde with fair to high stereoselectivity depending on the aldehyde substrate. Aromatic dialdehydes react with bis-boro-butadienes creating three new stereocenters with usually high diastereoselectivity.