2016
DOI: 10.1016/j.tet.2015.12.052
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Towards the enantioselective synthesis of axially chiral cyclic bis(bibenzyls) through sulfoxide-controlled diastereoselective Suzuki coupling

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Cited by 10 publications
(6 citation statements)
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“…The potential of a sulfoxide moiety has been reported in the atropo‐diastereoselective Suzuki–Miyaura coupling reactions, as well as by us in the field of bis(bibenzyls) . Regarding the excellent ortho ‐directing effect of the enantiopure sulfinyl group, which was extensively investigated in Colobert's group for enantiopure biaryls, we speculated that this auxiliary could now be used for the first atroposelective total synthesis of enantiopure isoplagiochin D ( 1 ).…”
Section: Figurementioning
confidence: 93%
See 1 more Smart Citation
“…The potential of a sulfoxide moiety has been reported in the atropo‐diastereoselective Suzuki–Miyaura coupling reactions, as well as by us in the field of bis(bibenzyls) . Regarding the excellent ortho ‐directing effect of the enantiopure sulfinyl group, which was extensively investigated in Colobert's group for enantiopure biaryls, we speculated that this auxiliary could now be used for the first atroposelective total synthesis of enantiopure isoplagiochin D ( 1 ).…”
Section: Figurementioning
confidence: 93%
“…[24] Thep otential of as ulfoxide moiety has been reported in the atropo-diastereoselective Suzuki-Miyaura coupling reactions, [25] as well as by us in the field of bis(bibenzyls). [26] Regarding the excellent ortho-directing effect of the enantiopure sulfinyl group,w hich was extensively investigated in Colobertsg roup for enantiopure biaryls, [27] we speculated that this auxiliary could now be used for the first atroposelective total synthesis of enantiopure isoplagiochin D(1). The atropo-diastereoselective macrocyclization step (4!5) should allow at otal control of the axial chirality of the biaryl axis a through Heck coupling cyclization of an iodine precursor (Scheme 1b).…”
mentioning
confidence: 99%
“…Six years later, the same group developed an elegant chiral sulfinyl group induced diastereoselective Heck macrocyclization of iodide 7 (Scheme 1b). [ 31‐34 ] Pleasingly, high yield (80%) and high diastereoselectivity (de 98%) have been achieved, although the modification of sulfinyl group to…”
Section: Background and Originality Contentmentioning
confidence: 99%
“…[24] Über das Potential von Sulfoxid-Gruppen in hoch atropdiastereoselektiven Suzuki-Miyaura-Kupplungen wurde kürzlich berichtet, [25] auch von uns im Kontext von Bis(bibenzylen). [26] In Anbetracht des exzellenten ortho'-dirigierenden Effekts der enantiomerenreinen Sulfinylgruppe -i n der Gruppe Colobert fürenantiomerenreine Biaryle intensiv untersucht [27] -hofften wir, dass dieses Auxiliar jetzt auch zur ersten atropselektiven Totalsynthese von enantiomerenreinem Isoplagiochin D( 1)e insetzbar wäre.D er atrop-diastereoselektive Makrocyclisierungsschritt (4 ! 5)s ollte eine optimale Kontrolle der axialen Chiralitätd er Biarylachse a bei der Heck-Cyclisierung eines Iodpräkursors erlauben (Schema 1b).…”
Section: Cyclophane Sind Gespannte Moleküled Ie Aromatischeunclassified
“…Andere chirale Liganden (PHOX, [17] Thre-PHOX [18] und Simple-PHOX [19] )f ührten nicht zur Cyclisierung oder ergaben niedrigere Atropselektivitäten wie (M)-SEGPhos [20] oder (M)-MeO-BIPHEP. [26] In Anbetracht des exzellenten ortho'-dirigierenden Effekts der enantiomerenreinen Sulfinylgruppe -i n der Gruppe Colobert fürenantiomerenreine Biaryle intensiv untersucht [27] -hofften wir, dass dieses Auxiliar jetzt auch zur ersten atropselektiven Totalsynthese von enantiomerenreinem Isoplagiochin D( 1)e insetzbar wäre.D er atrop-diastereoselektive Makrocyclisierungsschritt (4 ! [24] Über das Potential von Sulfoxid-Gruppen in hoch atropdiastereoselektiven Suzuki-Miyaura-Kupplungen wurde kürzlich berichtet, [25] auch von uns im Kontext von Bis(bibenzylen).…”
unclassified