Chiral carbanions, part 4: Borylation of (trimethylsilyl)methyl N,N-dialkyl-carbamates - Diastereoselectivity and structural studies
- Author(s)
- Biljana Peric Simov, Lothar Brecker, Gerald Giester, Friedrich Hammerschmidt
- Abstract
(Trimethylsilyl)methyl carbamates were prepared from (trimethylsilyl) methanol and N,N-dialkylcarbamoyl chlorides and were metalated by s-BuLi/TMEDA. The configurationally labile lithiated carbamates were reacted with borates derived from (+)-pinane-2,3-diol to give boronates diastereoselectively (yields up to 84%, dr up to 17:1). The absolute configurations at the boron-bearing carbon atoms of three boronates were assigned by single crystal X-ray structure analyses.
- Organisation(s)
- Department of Organic Chemistry, Department of Mineralogy and Crystallography
- External organisation(s)
- University of Vienna
- Journal
- Synthesis: journal of synthetic organic chemistry
- Pages
- 2704-2710
- No. of pages
- 7
- ISSN
- 0039-7881
- Publication date
- 2004
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 1051 Geology, Mineralogy
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/5f69e4f8-08c7-45e5-8cd2-da77cc61bbf1