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Title: Enantioselective Lactonization by π‐Acid‐Catalyzed Allylic Substitution: A Complement to π‐Allylmetal Chemistry
Abstract

Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non‐racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π‐acid catalysis. More specifically, a catalytic enantioselective dehydrative lactonization of allylic alcohols using a novel PdII‐catalyst containing the imidazole‐basedP,N‐ligand (S)‐StackPhos is reported. The high‐yielding reactions are operationally simple to perform with enantioselectivities up to 99 %ee. This strategy facilitates the replacement of a poor leaving group with what would ostensibly be a better leaving group in the product avoiding complications arising from racemization by equilibration.

 
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NSF-PAR ID:
10305036
Author(s) / Creator(s):
 ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Angewandte Chemie International Edition
Volume:
60
Issue:
41
ISSN:
1433-7851
Format(s):
Medium: X Size: p. 22224-22229
Size(s):
p. 22224-22229
Sponsoring Org:
National Science Foundation
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