1-Alkoxyamino-2-nitroalkanes as Key Building Blocks for a Chemo- and Diastereoselective Synthesis of a New Type of Polyfunctionalized N-Alkoxypiperidine

✍ Scribed by M. Ángeles López-García; Inés Maya; José G. Fernández-Bolaños; Giovanna Bosica; Roberto Ballini

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 262 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201000540

✦ Synopsis

Abstract

A highly efficient conversion of β‐nitrostyrenes into a new kind of functionalized N‐alkoxy‐2‐hydroxypiperidine in two steps was developed, giving excellent yields and diastereoselectivity. The prepared compounds are the first examples of N‐alkoxy‐2‐hydroxypiperidines. The synthetic approach involved the conjugate addition of alkoxyamines to β‐nitrostyrenes, followed by Michael addition of the isolated nitroalkoxyamines to α,β‐unsaturated carbonyl compounds, and intramolecular addition of the alkoxyamino group to the carbonyl functionality of the (non‐isolated) adducts. Although three stereogenic centers are formed, only one diastereoisomer was detected. This unprecedented sequence of reactions can also be performed in a one‐pot fashion.