Unknown

Dataset Information

0

?,?-Unsaturated Gold(I) Carbenes by Tandem Cyclization and 1,5-Alkoxy Migration of 1,6-Enynes: Mechanisms and Applications.

ABSTRACT: 1,6-Enynes bearing OR groups at the propargyl position generate ?,?-unsaturated gold(I)-carbenes/ gold(I) stabilized allyl cations that can be trapped by alkenes to form cyclopropanes or 1,3-diketones to give products of ?-alkylation. The best migrating group is p-nitrophenyl ether, which leads to the corresponding products without racemization. Thus, an improved formal synthesis of (+)-schisanwilsonene A has been accomplished. The different competitive reaction pathways have been delineated computationally.

SUBMITTER: Calleja P 

PROVIDER: S-EPMC5132047 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

α,β-Unsaturated Gold(I) Carbenes by Tandem Cyclization and 1,5-Alkoxy Migration of 1,6-Enynes: Mechanisms and Applications.

Calleja Pilar P   Pablo Óscar Ó   Ranieri Beatrice B   Gaydou Morgane M   Pitaval Anthony A   Moreno María M   Raducan Mihai M   Echavarren Antonio M AM  

Chemistry (Weinheim an der Bergstrasse, Germany) 20160816 38

1,6-Enynes bearing OR groups at the propargyl position generate α,β-unsaturated gold(I)-carbenes/ gold(I) stabilized allyl cations that can be trapped by alkenes to form cyclopropanes or 1,3-diketones to give products of α-alkylation. The best migrating group is p-nitrophenyl ether, which leads to the corresponding products without racemization. Thus, an improved formal synthesis of (+)-schisanwilsonene A has been accomplished. The different competitive reaction pathways have been delineated com  ...[more]

Similar Datasets

Unknown Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes.
| S-EPMC6657412 | biostudies-literature
Unknown Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes.
| S-EPMC3817472 | biostudies-literature
Unknown Gold-catalyzed enantioselective ring-expanding cycloisomerization of cyclopropylidene bearing 1,5-enynes.
| S-EPMC3998771 | biostudies-literature
Unknown Gold(i)-catalyzed addition of aldehydes to cyclopropylidene bearing 6-aryl-1,5-enynes.
| S-EPMC5134929 | biostudies-literature
Unknown Enantioselective Alkoxycyclization of 1,6-Enynes with Gold(I)-Cavitands: Total Synthesis of Mafaicheenamine C.
| S-EPMC8251978 | biostudies-literature
Unknown Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes.
| S-EPMC5911161 | biostudies-literature
Unknown Rh(I)-Catalyzed Cycloisomerization of 1,6-Enynes.
| S-EPMC4655000 | biostudies-literature
Unknown Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones.
| S-EPMC3201045 | biostudies-other
Unknown C-C Bond Migration in the Cycloisomerization of 1,6-Enynes.
| S-EPMC5321652 | biostudies-literature
Unknown A racemic formal total synthesis of clavukerin A using gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes as the key strategy.
| S-EPMC3135252 | biostudies-literature