Copper-Catalyzed Desymmetric Intramolecular Ullmann C–N Coupling: An Enantioselective Preparation of Indolines

The first highly enantioselective copper-catalyzed intramolecular Ullmann C–N coupling reaction has been developed. The asymmetric desymmetrization of 1,3-bis­(2-iodoaryl)­propan-2-amines catalyzed by CuI/(R)-BINOL-derived ligands led to the enantioselective formation of indolines in high yields and excellent enantiomeric excesses. This method was also applied to the formation of 1,2,3,4-tetrahydroquinolines in high yields and excellent enantioselectivity

Copper-Catalyzed Desymmetric Intramolecular Ullmann C–N Coupling: An Enantioselective Preparation of Indolines

The first highly enantioselective copper-catalyzed intramolecular Ullmann C–N coupling reaction has been developed. The asymmetric desymmetrization of 1,3-bis­(2-iodoaryl)­propan-2-amines catalyzed by CuI/(R)-BINOL-derived ligands led to the enantioselective formation of indolines in high yields and excellent enantiomeric excesses. This method was also applied to the formation of 1,2,3,4-tetrahydroquinolines in high yields and excellent enantioselectivity

Area under the receiver operating characteristic curve (AUC) for MSKCC, SOC, and PKUPH models (n = 80).

<p>Area under the receiver operating characteristic curve (AUC) for MSKCC, SOC, and PKUPH models (n = 80).</p

Area under the receiver operating characteristic curve (AUC) for MSKCC, SOC, and PKUPH models (n = 40).

<p>Area under the receiver operating characteristic curve (AUC) for MSKCC, SOC, and PKUPH models (n = 40).</p

Multivariable logistic regression of clinicopathologic data and NSLN involvement (n = 80).

<p><i>S.E</i>: Standard error.</p><p><i>OR:</i> Odds ratio.</p><p>CI: Confidence intervals.</p

Univariate analyses for patient and tumor and SLN characteristics associated with NSLN metastases (n = 80).

<p>*M:Median, Q25:25% of Quartile, Q75:75% of Quartile.</p

MSKCC and SOC Models at 10% Predicted Probability Cut-off Values Applied to PKUPH Data (n = 120).

<p>MSKCC and SOC Models at 10% Predicted Probability Cut-off Values Applied to PKUPH Data (n = 120).</p

Clinical data of patients with positive SLNs from MSKCC, SOC and PKUPH.

<p>Clinical data of patients with positive SLNs from MSKCC, SOC and PKUPH.</p

MSKCC, SOC and PKUPH Models at 10% Predicted Probability Cutoff Values Applied to PKUPH Data (n = 40).

<p>MSKCC, SOC and PKUPH Models at 10% Predicted Probability Cutoff Values Applied to PKUPH Data (n = 40).</p