Synthesis of (±)-3,3′-diphenyl-2,2′-binaphthol via different routes using Pd and Ni as catalyst respectively
3,3′-Biphenyl-2,2′-binaphthols (BINOLs) are precursors of phosphoric acids that are widely used as ligands and catalysts in organic reactions. In this report, two routes for the synthesis of (±)-3,3′-diphenyl BINOLs via (±)-3,3′ bis-halogenated BINOLs int
Fu, Zhengjiang,Cao, Xihan,Hao, Guangguo,Shi, Quanqing,Cai, Hu
p. 831 - 836
(2020/09/09)
Asymmetric allylboration of aldehydes and ketones using 3,3′-disubstitutedbinaphthol-modified boronates
Allylboronates derived from 3,3′-disubstituted 2,2′-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness.
Wu, T. Robert,Shen, Lixin,Chong, J. Michael
p. 2701 - 2704
(2007/10/03)
Design of bronsted acid-assisted chiral Lewis acid (BLA) catalysts for highly enantioselective Diels-Alder reactions
Bronsted acid-assisted chiral Lewis acid (BLA) was highly effective as a chiral catalyst for the enantioselective Diels-Alder reaction of both α- substituted and α-unsubstituted α,β-enals with various dienes. Hydroxy groups in optically active binaphthol derivatives and boron reagents with electron-withdrawing substituents were used as Bronsted acids and Lewis acids, respectively. Intramolecular Bronsted acids in a chiral BLA catalyst played an important role in accelerating the rate of Diels-Alder reactions and in producing a high level of enantioselectivity. In particular, excellent enantioselectivity was achieved due to intramolecular hydrogen bonding interaction and attractive π-π donor-acceptor interaction in the transition-state assembly by hydroxy aromatic groups in a chiral BLA catalyst.