Annulations of enantioenriched allenylsilanes with in situ generated iminium ions: stereoselective synthesis of diverse heterocycles.

Org Lett

Department of Chemistry, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.

Published: January 2009

Highly enantioenriched allenylsilanes participate in Lewis acid mediated annulations with in situ generated iminium ions derived from tert-butyl carbamate and methyl carbamate to selectively form functionalized 4,5-dihydropyrroles and 4,5-dihyrooxazines, respectively. The dihydropyrrole products were further elaborated in a stereocontrolled vinylsilane terminated cyclization with in situ generated oxonium ions, resulting in pyranopyrroles.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3164280PMC
http://dx.doi.org/10.1021/ol802618pDOI Listing

Publication Analysis

Top Keywords

situ generated
12
enantioenriched allenylsilanes
8
generated iminium
8
iminium ions
8
annulations enantioenriched
4
allenylsilanes situ
4
ions stereoselective
4
stereoselective synthesis
4
synthesis diverse
4
diverse heterocycles
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!