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Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
Author(s) -
Schmidt Johannes P.,
Breit Bernhard
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009166
Subject(s) - rhodium , enantioselective synthesis , stereoselectivity , catalysis , chemistry , combinatorial chemistry , stereochemistry , terminal (telecommunication) , compatibility (geochemistry) , computer science , organic chemistry , computer network , engineering , chemical engineering
A comprehensive study of a diastereoselective Rh‐catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn ‐selective access to synthetically important 2,4‐disubstituted and 2,4,6‐trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional‐group compatibility and the enantioselective total synthesis of (−)‐centrolobine.