Diastereoselective synthesis of vicinal amino alcohols

Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines – development of a phosphite-driven cyclodehydration

“…1) represent a frequent core motif of many pharmacologically active natural products [1–9], chiral auxiliaries [10–11] and catalysts for asymmetric synthesis [12–14]. Especially the 2-substituted 3-hydroxypiperidine scaffold of the general structure B (as one type of an 1,2-amino alcohol) can be found in numerous natural products and other bioactive compounds [1–7]. Selected examples are given in Fig.…”

Harmicine, a Tetracyclic Tetrahydro-β-Carboline: From the First Synthetic Precedent to Isolation from Natural Sources to Target-Oriented Synthesis (Review)*

“…As a solution, the 9-phenylfluoren-9-yl (Pf) protecting group strategy was developed as an alternative to the previously employed, acid-labile trityl group [85,86]. There are other means to prevent racemization in said substrates, but those methods typically require the use of double nitrogen protecting groups (for representative examples, see [87]). To expand the utility of the Pf protecting group strategy, we sought a procedure to synthesize chiral THβC by transferring the amino acid side chain to the THβC C-1 position.…”

Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

“…We have recently reviewed the literature on the synthesis of 1,2-vicinal amino alcohols [53]. Use of Garner’s aldehyde for the synthesis of non-natural amino acids through ethynylglycine has been reviewed [54].…”