Stereoselective Traceless Borylation-Allenation of Propargylic Epoxides: Dual Role of the Copper Catalyst.

Carlos Jarava-BarreraAlejandro ParraLaura AmenósAna ArroyoMariola Tortosa

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2017)

Chiral α-allenols are prepared with high diastereocontrol through an unprecedented and spontaneous β-oxygen elimination of an α-epoxy vinyl boronate. Stochiometric experiments and DFT calculations support a dual role of the copper catalyst, which orchestrates the hydroboration and the syn-elimination step.

Keyphrases

ionic liquid
density functional theory
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molecular dynamics
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molecular dynamics simulations
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