Asymmetric organocatalytic anthrone additions to activated alkenes

Effective asymmetric Michael addition of anthrone to nitroalkenes using chiral tetraoxacalix[2]arene[2]triazines as organocatalysts

“…Expanding the research beyond to heteroaromatic nitroalkene, the reaction was again achieved in both circumstances with satisfactory yield and enantioselectivity values ( Table 3, entry 10). This stereochemical result can be accommodated by a qualitative model related to that proposed by Zea et al 34 for the addition of anthrone to β-nitrostyrene as shown in Figure 1. In this model, the secondary amine in the catalyst reacts the anthrone enolate oxygen.…”

“…This stereochemical result can be accommodated by a qualitative model related to that proposed by Zea et al for the addition of anthrone to β‐ nitrostyrene as shown in Figure . In this model, the secondary amine in the catalyst reacts the anthrone enolate oxygen.…”

Chiral primary amino alcohol organobase catalysts for the asymmetric Diels–Alder reactions of anthrones with maleimides

“…Although bulkier N-benzylmaleimide 10c also did not afford the 11c 9 also afforded the corresponding DA adducts 11e 10a ,f 10a respectively, in excellent chemical Table 3 The…”

“…A solution of amino alcohol 2e (358 mg, 1 mmol) in CH were known compounds and were identified by spectral data which were in good agreement with those reported. [2][3][4][5][6][7][8][9]…”

“…2 Particularly, the DA reaction of anthrone with N-substituted maleimide 3 to construct a cage anthrone derivatives, which are key intermediates for the preparations of some unsaturated lactams with antipsoriatic and antiproliferative biological activities, have been studied extensively. 4 Several efficient chiral organobases such as cinchona alkaloids, 5 pyrrolidine derivatives, 6 cyclic guanidines, 7 bisoxazolines, 8 and tertiary amine thioureas 9 have been used to promote those reactions (Scheme 1). 10 However, to the best of our knowledge, the effectiveness of primary β-amino alcohol 11 organocatalyst as an organobase in this reaction has not been shown yet.…”