Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 20, Pages 7414-7417Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja401709k
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Funding
- UT Southwestern Endowed Scholars in Biomedical Research Program
- Robert A. Welch Foundation [I-1764)]
- ACS-PRF [51707-DNI1]
- American Cancer Society & Simmons Cancer Center Institutional Research Grant [ACS-IRG 02-196]
- BYU
- Fulton Super-computing Lab
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Herein we disclose an organocatalytic aryl aryl bond-forming process for the regio- and atroposelective synthesis of 2,2'-diamino-1,1'-binaphthalenes (BINAMs). In the presence of catalytic amounts of axially chiral phosphoric acids, achiral N,N'-binaphthyl hydrazines undergo a facile [3,3]-sigmatropic rearrangement to afford enantiomerically enriched BINAM derivatives in good to excellent yield. This transformation represents the first example of a metal-free, catalytic C(sp(2)) C(sp(2)) bond formation between two aromatic rings with concomitant de novo atroposelective installation of an axis of chirality. Density functional calculations reveal that, in the transition state for C-C bond formation, the phosphoric acid proton of the catalyst is fully transferred to one of the N-atoms of the substrate, and the resulting phosphate acts as a chiral counterion.
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