3 years ago
Catalytic Asymmetric Roskamp Reaction of Silyl Diazoalkane: Synthesis of Enantioenriched α-Silyl Ketone
Jae Yeon Kim, Do Hyun Ryu, Byung Chul Kang
A catalytic enantioselective Roskamp reaction of silyl diazoalkane to synthesize a highly optically active α-silyl ketone from aldehydes is described. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction provides α-chiral silyl ketones with good yields (up to 97%) and high enantioselectivities (up to >99% ee). In addition, a one-pot procedure using an asymmetric Roskamp/reduction strategy gives highly optically active syn-β-hydroxysilane in good yields (up to 94%) with high enantioselectivities (up to 99% ee) and syn stereoselectivities (>20:1).
Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02928
DOI: 10.1021/acs.orglett.7b02928
You might also like
Never Miss Important Research
Researcher is an app designed by academics, for academics. Create a personalised feed in two minutes.
Choose from over 15,000 academics journals covering ten research areas then let Researcher deliver you papers tailored to your interests each day.
Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.