Enantioselective Aza-Heck Cyclizations of N-(Tosyloxy)carbamates: Synthesis of Pyrrolidines and Piperidines

Xiaofeng Ma; Ian R Hazelden; Thomas Langer; Rachel H Munday; John F Bower

doi:10.1021/jacs.8b12689

Enantioselective Aza-Heck Cyclizations of N-(Tosyloxy)carbamates: Synthesis of Pyrrolidines and Piperidines

J Am Chem Soc. 2019 Feb 27;141(8):3356-3360. doi: 10.1021/jacs.8b12689. Epub 2019 Feb 18.

Authors

Xiaofeng Ma¹, Ian R Hazelden¹, Thomas Langer², Rachel H Munday², John F Bower¹

Affiliations

¹ School of Chemistry , University of Bristol , Bristol , BS8 1TS , United Kingdom.
² Pharmaceutical Technology & Development , AstraZeneca , Charter Way , Macclesfield , SK10 2NA , United Kingdom.

PMID: 30775918
DOI: 10.1021/jacs.8b12689

Abstract

Pd(0)-systems modified with SPINOL-derived phosphoramidate ligands promote highly enantioselective aza-Heck cyclizations of alkenyl N-(tosyloxy)carbamates. The method provides versatile access to challenging N-heterocycles and represents the broadest scope enantioselective aza-Heck protocol developed to date.

Publication types

Research Support, Non-U.S. Gov't