Abstract
Pyrrolidin-2-ones are important heterocyclic motifs
found in natural products and biologically active
synthetic molecules. Addition of nucleophiles, incl
uding allylsilanes, isonitriles and organometallics
, to
N
-
acyliminium ions represents one of the most commonl
y used approaches for the formation of substituted
pyrrolidin-2-ones. Only few studies on the nucleoph
ic addition of organoboronic acids to
N
-acyliminium
ions have been reported. Herein, we disclose our re
cent efforts for the synthesis of substituted pyrro
lidin-
2-ones through Lewis-acid-mediated Petasis-type rea
ctions. By implementing a reductive cyclization
reaction, linear
L
-malic acid derivatives were rapidly converted into
cyclic
N
-acyliminium ions. Under the
optimized conditions, entailing the use of HFIP as
solvent, both electron-rich and electron-deficient
boronic
acids were successfully added to a range of cyclic
N
-acyliminium ions, typically with excellent
diastereoselectivity with electron-deficient boroni
c acids.
Original language | English |
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Journal | ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY |
ISSN | 0065-7727 |
Publication status | Published - 2014 |
Event | 248th National Fall Meeting of the American Chemical Society - San Francisco, United States Duration: 10 Aug 2014 → 14 Aug 2014 Conference number: 248 |
Conference
Conference | 248th National Fall Meeting of the American Chemical Society |
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Number | 248 |
Country/Territory | United States |
City | San Francisco |
Period | 10/08/2014 → 14/08/2014 |