1986
DOI: 10.1021/ja00263a020
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Chiral allenylboronic esters as practical reagents for enantioselective carbon-carbon bond formation. Facile synthesis of (-)-ipsenol

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Cited by 150 publications
(47 citation statements)
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“…Our initial screening studies found that previously reported enantioselective methods based on organoboron reagents gave sluggish reactivity and low diastereomeric ratio (d.r. typically <3:1) . We found allenylindium along with chiral aminoalcohol ligand could afford the desired product with a d.r.…”
Section: Methodsmentioning
confidence: 84%
“…Our initial screening studies found that previously reported enantioselective methods based on organoboron reagents gave sluggish reactivity and low diastereomeric ratio (d.r. typically <3:1) . We found allenylindium along with chiral aminoalcohol ligand could afford the desired product with a d.r.…”
Section: Methodsmentioning
confidence: 84%
“…Erstaunlicherweise ließen sich tertiäre Propargylalkohole mit dieser Strategie mit vollständiger Regiokontrolle in die entsprechenden Allenylboronsäureester überführen, die wertvolle Reagenzien für die Synthese von homopropargylischen Alkoholen und Aminen sind . Dies ist der erste radikalische Ansatz zur Synthese dieser wichtigen Substanzklasse .…”
Section: Methodsunclassified
“…To further expand the scope of this tandem reaction we considered the use of the more versatile propargylic systems 18. Further investigation was, therefore, aimed at the tandem reaction of α‐epoxy alcohols with allenylboronic acid (RB(OH) 2 , R=allenyl),19 and the cyclic substrates ( 1 a , 1 f , , and 1 k R 4 =alkyl) and the acyclic one ( 1 h , R 4 =H) were subjected to the reaction sequence. The 1‐progargyl‐2‐quaternary‐1,3‐diols were obtained in moderate yields.…”
Section: Methodsmentioning
confidence: 99%