The endo-aza-Michael addition in the synthesis of piperidines and pyrrolidines

• Main Authors: Bates, Roderick Wayland, Ko, Weiting, Barát, Viktor
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Chemistry; Aza-Michael Addition; Synthesis (Chemical)
• Online Access: https://hdl.handle.net/10356/141239
• Institution: Nanyang Technological University

Intramolecular endo-aza-Michael additions are categorised in various ways. Firstly whether they are single or double reactions, secondly whether they are endo- or exo-activated (or both), thirdly whether the Michael acceptor is an alkene or an alkyne, and finally whether the product is a six or a five membered ring. Reactions in the various categories are illustrated by syntheses of piperidines and pyrrolidines, including a range of natural products. The question of the stereochemical outcome and whether it is understood is discussed.