Issue 34, 2014

Asymmetric semipinacol rearrangement of 2,3-allenols with N-bromo-1,8-naphthalimide

Abstract

A method using quinidine and optically active binol-derived phosphoric acid as a cocatalyst to catalyze the asymmetric semipinacol rearrangement of 2,3-allenols forming optically active 3-bromo-3-enals that contain an all-carbon quaternary stereocenter has been developed. After some further treatments, the products with practical enantiomeric purity could be prepared.

Graphical abstract: Asymmetric semipinacol rearrangement of 2,3-allenols with N-bromo-1,8-naphthalimide

Supplementary files

Article information

Article type
Communication
Submitted
28 Jan 2014
Accepted
25 Feb 2014
First published
26 Feb 2014

Chem. Commun., 2014,50, 4445-4447

Asymmetric semipinacol rearrangement of 2,3-allenols with N-bromo-1,8-naphthalimide

B. Guo, C. Fu and S. Ma, Chem. Commun., 2014, 50, 4445 DOI: 10.1039/C4CC00767K

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