53834-74-5Relevant academic research and scientific papers
Nickel-Catalyzed Desymmetric Hydrogenation of Cyclohexadienones: An Efficient Approach to All-Carbon Quaternary Stereocenters
You, Cai,Li, Xiuxiu,Gong, Quan,Wen, Jialin,Zhang, Xumu
supporting information, p. 14560 - 14564 (2019/10/11)
Nickel-catalyzed desymmetric hydrogenation has been achieved. With the Ni(OTf)2/(S,S)-Ph-BPE system, a series of ?,?-disubstituted cyclohexadienones were transformed to the corresponding cyclohexenones with a chiral all-carbon quaternary center at the γposition in high yields (92-98%) and excellent enantioselectivities (92%-99% ee). This catalytic system can also tolerate the desymmetric reaction of spirocarbocyclic cyclohexadienones to produce the corresponding cyclohexenones bearing a chiral spiro quaternary carbon with high yields (94%-98%) and ee values (96%-99% ee). Furthermore, this methodology provides an efficient and concise synthetic route to the intermediate of natural products cannabispirenones A and B.
Asymmetric Synthesis of Remote Quaternary Centers by Copper-Catalyzed Desymmetrization: An Enantioselective Total Synthesis of (+)-Mesembrine
Bokka, Apparao,Mao, James X.,Hartung, John,Martinez, Steven R.,Simanis, Justin A.,Nam, Kwangho,Jeon, Junha,Shen, Xiaoqiang
, p. 5158 - 5162 (2018/09/13)
Catalytic asymmetric syntheses of remote quaternary stereocenters have been developed by copper-catalyzed 1,4-hydrosilylation of ?,?-disubstituted cyclohexadienones. A variety of cyclohexenones have been synthesized in good yield and excellent enantioselectivity. Versatile 2-silyloxy diene intermediates bearing ?,?-disubstituted all carbon stereogenic centers can be isolated from the mild reaction conditions. The utility of this strategy is exemplified in a catalytic asymmetric total synthesis of (+)-mesembrine.
Catalytic Desymmetrizing Dehydrogenation of 4-Substituted Cyclohexanones through Enamine Oxidation
Zhu, Lihui,Zhang, Long,Luo, Sanzhong
supporting information, p. 2253 - 2258 (2018/02/09)
A desymmetrizing dehydrogenation process catalyzed by a chiral primary amine is described herein. The reaction proceeds through the oxidation of a ketone enamine by IBX and enables the highly enantioselective desymmetrization of 4-substituted cyclohexanones with the generation of chiral 4-substituted cyclohexenones containing a remote γ-stereocenter.
Asymmetric Induction at Remote Quaternary Centers of Cyclohexadienones by Rhodium-Catalyzed Conjugate Hydrosilylation
Naganawa, Yuki,Kawagishi, Mayu,Ito, Jun-Ichi,Nishiyama, Hisao
, p. 6873 - 6876 (2016/06/13)
The enantioselective desymmetrizing conjugate hydrosilylation of prochiral differently γ,γ-disubstituted cyclohexadienone derivatives 2 to furnish the corresponding cyclohexenones 4 with a remote chiral all-carbon quaternary center at the γ position is de
A new powerful strategy for the organocatalytic asymmetric construction of a quaternary carbon stereogenic center
Lnokoishi, Yogo,Sasakura, Niiha,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
supporting information; experimental part, p. 1616 - 1619 (2010/06/17)
(Figure Presented) A new method for chiral diamine-catalyzed Robinson-type annulation was developed to construct cyclohexenone derivatives bearing a quaternary carbon stereogenic center at the 4-position in high enantiomeric excess. This method was successfully applied to the short synthesis of (+)-sporochnol A.
Construction of a Chiral Quaternary Carbon Center by Enantioselective Deprotonation: Application to the Formal Synthesis of (+)-α-Cuparenone
Honda, Toshio,Kimura, Nobuaki,Tsubuki, Masayoshi
, p. 21 - 24 (2007/10/02)
Construction of a chiral quaternary carbon center was achieved by employing an enantioselective deprotonation with chiral bases and this strategy was applied to the formal synthesis of (+)-α-cuparenone.
An Asymmetric Isoxazole Annulation
Marron, Brian E.,Schlicksupp, Ludwig,Natale, N. R.
, p. 1067 - 1070 (2007/10/02)
An asymmetric isoxazole annulation proceeds from the (S)-O-methoxyphenylalaninol imine of (RS)-2-phenylpropionaldehyde (3).Deprotonation, quenching with 4-chloromethyl-3,5-dimethylisoxazole, and hydrolysis produced isoxazolylaldehyde (5), whose structure
