An asymmetric synthesis of a silicon-containing proline surrogate, N-Boc-(R)-silaproline (1), is described. Starting from N-Boc-dehydroalanine ester, deprotonation, followed by N-alkylation with chloromethyldimethylsilane under flow conditions, afforded the N-alkylated product 8 in 91% yield. An unprecedented enantioselective (NBD)2RhBF4/Josiphos 404-1 catalyzed 5-endo-trig hydrosilylation afforded the silaproline ester in 85-90% yield and &gt;95% ee. Subsequent saponification, and salt formation upgraded 1 to &gt;99% ee.

Asymmetric synthesis of N-Boc-(R)-silaproline via Rh-catalyzed intramolecular hydrosilylation of dehydroalanine and continuous flow N-alkylation

256th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.