Asymmetric routes to substituted piperidines

Abstract

The piperidine ring is the commonest heterocyclic subunit of natural products, and is a key part of numerous drugs. This article identifies the best asymmetric routes to the piperidine ring system, emphasising methods that are efficient, reliable and flexible. The cover picture shows the plant poison hemlock, which is a source of many piperidine alkaloids such as coniine.

Preparation and Reaction of Titania Particles Encapsulated in Hollow Silica Shells as an Efficient Photocatalyst for Stereoselective Synthesis of Pipecolinic Acid

“…The composite possesses size-selective properties in the photodecomposition of organic compounds; SiO 2 /void/TiO 2 showed photocatalytic activity for decomposition of small substrates retaining the activity of original bare TiO 2 , while negligible activity for polymers was observed, i.e., SiO 2 /void/TiO 2 exhibits molecular size selectivity. Recently, we have attempted to use the SiO 2 /void/TiO 2 photocatalyst for the synthesis of Lpipecolinic acid (L-PCA), a useful intermediate material for various fine chemicals, 11 and found another function of silica shell to improve stereoselectivity, instead of molecular-size selectivity and report here.…”

One-Pot Two-Step Organocatalytic Asymmetric Synthesis of Spirocyclic Piperidones via Wolff Rearrangement–Amidation–Michael–Hemiaminalization Sequence

“…Using benzenesulfonyl-and methylsulfonyl-substituted primary amines provided the expected 98 spiro-products 5r and 5s (entries [18][19]. In terms of the alkyl primary amine, benzyl was also 99 compatible with this reaction system, generating the products 5t in good results (entry 20).…”

Asymmetric synthesis of N-protected 3-methylpiperidin-2-one and its diastereoisomer

“…Piperidin-2-one is a versatile building block for the synthesis of piperidine and piperidone derivatives (Bailey et al, 1998;Baussanne et al, 1998), a large variety of bioactive moieties (Kosugi et al, 2012;Wang et al, 2013;Jadav et al, 2014;Zarate et al, 2014) as well as medicines to treat diseases like inflammatory bowel disease (Old et al, 2005) and neurodegenerative diseases (Cohen and Patel, 2014). 5-substituted 1-methyl-2-pyridones, which are one kind of piperidone derivative, have been evaluated as active agents against benign prostatic hyperplasia (BPH) and prostate cancer (Hartmann et al, 1994).…”