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Sequential Pd 0 ‐ and Pd II ‐Catalyzed Cyclizations: Enantioselective Heck and Nucleopalladation Reactions
Author(s) -
Whyte Andrew,
Bajohr Jonathan,
Arora Ramon,
Torelli Alexa,
Lautens Mark
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202106518
Subject(s) - enantioselective synthesis , alkyne , palladium , nucleophile , chemistry , catalysis , aryl , medicinal chemistry , combinatorial chemistry , organic chemistry , stereochemistry , alkyl
An enantioselective consecutive cyclization/coupling process, catalyzed by palladium is reported. Stereoinduction arises from an enantioselective carbopalladation, generating an intermediate which promotes a nucleopalladation step. The dual cyclization sequence was compatible with a variety of alkyne‐tethered oxygen‐ and nitrogen‐centered nucleophiles, and a variety of alkenyl‐tethered aryl iodides, to forge numerous bisheterocycles in good yields and high regio‐ and enantioselectivities.