Title:
|
Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
|
Author:
|
Zuccarello, Giuseppe; Mayans, Joan G.; Escofet, Imma; Scharnagel, Dagmar; Kirillova, Mariia S.; Pérez-Jimeno, Alba H.; Calleja, Pilar; Boothe, Jordan R.; Echavarren, Antonio M.
|
Abstract:
|
Chiral gold(I) catalysts have been designed based on a modi-fied JohnPhos ligand with a distal C2-2,5-diarylpyrrolidine that creates a tight binding cavity. The C2-chiral element is close to where the C-C bond formation takes place in cycliza-tions of 1,6-enynes. These chiral mononuclear catalysts have been applied for the enantioselective 5-exo-dig and 6-endo-dig cyclization of different 1,6-enynes as well as in the first enan-tioselective total synthesis of three members of the carexane family of natural products. Opposite enantioselectivities have been achieved in seemingly analogous reactions of 1,6-enynes, which result from different chiral folding of the substrates based on attractive aryl-aryl interactions. |
Publication date:
|
2017-07-10 |
Subject(s):
|
54 |
Rights:
|
You have selected the Attribution-NonCommercial-NoDerivatives 4.0 International License.
This license is permanently located at
http://creativecommons.org/licenses/by-nc-nd/4.0/. |
Pages:
|
11858 p. |
Document type:
|
Article Article - Accepted version |
DOI:
|
10.1021/jacs.9b06326
|
Share:
|
|