1351858-96-2Relevant academic research and scientific papers
Bidentate auxiliary-directed alkenyl C-H allylation: Via exo-palladacycles: Synthesis of branched 1,4-dienes
Shen, Cong,Lu, Xiunan,Zhang, Jian,Ding, Liyuan,Sun, Yaling,Zhong, Guofu
, p. 13582 - 13585 (2019/11/14)
An alkenyl C-H allylation by an exo-palladacycle intermediate is demonstrated, employing unactivated (Z)-Alkenes and allyl carbonates. With the use of an 8-Aminoquinoline (AQ) derived amide as the directing group, the N,N-bidentate-chelation-Assisted C-H activation protocol proceeded under mild and oxidant-free conditions with excellent selectivity. The utility of this approach is demonstrated by the preparative scale, selective conversion of inseparable Z/E alkenes and ready removal of the amide auxiliary to provide the corresponding ester.
Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis
Griffin, Jeremy D.,Cavanaugh, Cortney L.,Nicewicz, David A.
supporting information, p. 2097 - 2100 (2017/02/15)
Halofunctionalization of alkenes is a classical method for olefin difunctionalization. It gives rise to adducts which are found in many natural products and biologically active molecules, and offers a synthetic handle for further manipulation. Classically, this reaction is performed with an electrophilic halogen source and leads to regioselective formation of the halofunctionalized adducts. Herein, we demonstrate a reversal of the native regioselectivity for alkene halofunctionalization through the use of an acridinium photooxidant in conjunction with a copper cocatalyst.
Development and mechanism of an enantioselective bromocycloetherification reaction via Lewis base/chiral Bronsted acid cooperative catalysis
Denmark, Scott E.,Burk, Matthew T.
, p. 344 - 355 (2014/07/08)
The development of a binary catalyst system for bromocycloetherification, consisting of an achiral Lewis base and a chiral Bronsted acid, is described in detail. The results of preliminary kinetic studies are also presented. Chirality 26:343-354, 2013.
Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst
Tan, Chong Kiat,Le, Chencheng,Yeung, Ying-Yeung
, p. 5793 - 5795 (2012/08/08)
A facile, highly regio- and enantioselective amino-thiocarbamate-catalyzed bromolactonization of cis-1,2-disubstituted olefinic acids has been developed. The use of the enantio-enriched lactones in the synthesis of chiral synthetic intermediates is also demonstrated. 2012
Enantioselective bromocycloetherification by Lewis base/chiral Bronsted acid cooperative catalysis
Denmark, Scott E.,Burk, Matthew T.
, p. 256 - 259 (2012/03/10)
A binary catalyst system for the enantioselective bromocycloetherification of 5-arylpentenols is described. The combination of an achiral Lewis base and a chiral Bronsted acid affords good enantioselectivities for the cyclization of Z configured 5-arylpen
