1132755-87-3Relevant articles and documents
Iridium-Catalyzed Asymmetric Hydroarylation of Chromene Derivatives with Aromatic Ketones: Enantioselective Synthesis of 2-Arylchromanes
Sakamoto, Kana,Nishimura, Takahiro
, p. 2124 - 2128 (2019)
Catalytic asymmetric hydroarylation of 2H-chromenes with aromatic ketones was realized by use of a cationic iridium/chiral phosphine complex. The reaction proceeded via olefin isomerization, followed by enantioselective hydroarylation, thus giving 2-arylchromanes in high yields with high enantioselectivity. (Figure presented.).
Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids
Lu, Yanhui,Nakatsuji, Hidefumi,Okumura, Yukimasa,Yao, Lu,Ishihara, Kazuaki
, p. 6039 - 6043 (2018/05/14)
Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to α-Tocopherol, α-Tocotrienol, Daedalin A and Englitazone in short steps. Furthermore, a halogenated product with an unsaturated side chain may provide polycyclic adducts under radical cyclization conditions.
A Modular Synthesis of 2-Alkyl- and 2-Arylchromans via a Three-Step Sequence
Orr, Robert K.,Campeau, Louis-Charles,Chobanian, Harry R.,McCabe Dunn, Jamie M.,Pio, Barbara,Plummer, Christopher W.,Nolting, Andrew,Ruck, Rebecca T.
, p. 657 - 666 (2017/01/28)
A convergent three-step method for the synthesis of 2-substituted chromans is described. These results have been accomplished via the Heck coupling of readily accessible allylic alcohols and 2-iodophenols, followed by reduction and Mitsunobu cyclization. The utility and generality of this method is demonstrated through the synthesis of a series of 2-aryl-, 2-heteroaryl- and 2-alkylchromans, as well as an azachroman derivative. The asymmetric version of this approach via a Noyori-catalyzed ketone reduction and subsequent cyclization is likewise highlighted.