TY - JOUR
T1 - Accessing Functionalized Furans from Reacting Enynones and Enynals through Furyl Metal Carbenes
AU - Cho, Ho Jun
AU - Kim, Ju Hyun
N1 - Publisher Copyright:
© 2024 Wiley-VCH GmbH.
PY - 2024/4
Y1 - 2024/4
N2 - Enynones and enynals represent donor-type carbene precursors that efficiently form furyl metal carbenes via a catalytic intramolecular 5-exo-dig cyclization and rearrangement cascade, in a 100 % atom-economical manner, using various metals. These furyl metal carbenes have been successfully utilized in numerous carbene reactions, including metal carbene X−H insertion, cyclopropanations, metathesis, and cross-coupling, demonstrating a broad reaction scope and efficiency in constructing highly functionalized furans. Recent years have witnessed significant advancements in transformations involving furyl metal carbenes, especially in asymmetric carbene insertion reactions, domino reactions involving zwitterionic intermediates, various rearrangement strategies, and their application in synthesizing functional materials and drug candidates. In this review, we summarize recent progress in furyl metal carbene reactions generated from enynones and enynals, focusing on the synthesis of highly functionalized furans.
AB - Enynones and enynals represent donor-type carbene precursors that efficiently form furyl metal carbenes via a catalytic intramolecular 5-exo-dig cyclization and rearrangement cascade, in a 100 % atom-economical manner, using various metals. These furyl metal carbenes have been successfully utilized in numerous carbene reactions, including metal carbene X−H insertion, cyclopropanations, metathesis, and cross-coupling, demonstrating a broad reaction scope and efficiency in constructing highly functionalized furans. Recent years have witnessed significant advancements in transformations involving furyl metal carbenes, especially in asymmetric carbene insertion reactions, domino reactions involving zwitterionic intermediates, various rearrangement strategies, and their application in synthesizing functional materials and drug candidates. In this review, we summarize recent progress in furyl metal carbene reactions generated from enynones and enynals, focusing on the synthesis of highly functionalized furans.
KW - asymmetric catalysis
KW - donor-type carbene
KW - enynone/enynal
KW - furan synthesis
UR - http://www.scopus.com/inward/record.url?scp=85182489866&partnerID=8YFLogxK
U2 - 10.1002/ajoc.202300616
DO - 10.1002/ajoc.202300616
M3 - Review article
AN - SCOPUS:85182489866
SN - 2193-5807
VL - 13
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
IS - 4
M1 - e202300616
ER -