TY - JOUR
T1 - Gold-Catalyzed Addition of β-Oxo Enols at Tethered Alkynes via a Non-Conia-ene Pathway
T2 - Observation of a Formal 1,3-Hydroxymethylidene Migration
AU - Narode, Akshay Subhash
AU - Ho, Yeu Shiuan
AU - Cheng, Mu Jeng
AU - Liu, Rai Shung
N1 - Funding Information:
The authors thank the Ministry of Education (MOE 111QR001I5) and the National Science and Technology Council (NSTC 111-2634-F-007-007), Taiwan, for their financial support of this work.
Publisher Copyright:
© 2023 American Chemical Society.
PY - 2023/3/10
Y1 - 2023/3/10
N2 - With the relay process of Ag(I)/Au(I) catalysts, a one-pot synthesis of skeletally rearranged (1-hydroxymethylidene)indene derivatives from 2-alkynylbenzaldehydes and α-diazo esters is described. This cascade sequence involves Au(I)-catalyzed 5-endo-dig attack of highly enolizable aldehydes at the tethered alkynes, leading to carbocyclizations with a formal 1,3-hydroxymethylidene transfer. On the basis of density functional theory calculations, the mechanism likely involves formation of cyclopropylgold carbenes, followed by an appealing 1,2-cyclopropane migration.
AB - With the relay process of Ag(I)/Au(I) catalysts, a one-pot synthesis of skeletally rearranged (1-hydroxymethylidene)indene derivatives from 2-alkynylbenzaldehydes and α-diazo esters is described. This cascade sequence involves Au(I)-catalyzed 5-endo-dig attack of highly enolizable aldehydes at the tethered alkynes, leading to carbocyclizations with a formal 1,3-hydroxymethylidene transfer. On the basis of density functional theory calculations, the mechanism likely involves formation of cyclopropylgold carbenes, followed by an appealing 1,2-cyclopropane migration.
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U2 - 10.1021/acs.orglett.3c00504
DO - 10.1021/acs.orglett.3c00504
M3 - Article
C2 - 36861973
AN - SCOPUS:85149533410
SN - 1523-7060
VL - 25
SP - 1589
EP - 1594
JO - Organic Letters
JF - Organic Letters
IS - 9
ER -