Asymmetric Synthesis of N‑Boc‑(R)‑Silaproline via Rh-Catalyzed Intramolecular Hydrosilylation of Dehydroalanine and Continuous Flow N‑Alkylation

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 unp...

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Veröffentlicht in:	Organic letters 2016-04, Vol.18 (8), p.1812-1815
Hauptverfasser:	Chung, John Y. L, Shevlin, Michael, Klapars, Artis, Journet, Michel
Format:	Artikel
Sprache:	eng
Schlagworte:	Alanine - analogs & derivatives Alanine - chemistry Alkylation Catalysis Cyclization Organosilicon Compounds - chemical synthesis Organosilicon Compounds - chemistry Proline - analogs & derivatives Proline - chemical synthesis Proline - chemistry
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