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  • Highly enantioselective deracemization of linear and vaulted biaryl ligands.

Highly enantioselective deracemization of linear and vaulted biaryl ligands.

Organic letters (2003-05-24)
Yu Zhang, Siu-Man Yeung, Hongqiao Wu, Douglas P Heller, Chunrui Wu, William D Wulff
ABSTRACT

[reaction: see text] A copper-mediated deracemization of the vaulted biaryl ligands VANOL and VAPOL can be readily achieved in the presence of (-)-spartiene. The optimal procedure involves the in situ generation of copper(II) and leads to the reproducible formation of (S)-VANOL and (S)-VAPOL in greater than 99% ee from the racemates. This method is superior to existing procedures for BINOL (92% ee).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(R)-VAPOL, 97%
Sigma-Aldrich
(S)-VAPOL, 97%
Sigma-Aldrich
(R)-VANOL, 97%
Sigma-Aldrich
(S)-VANOL, 97%