Development of Enantioselective Nitrogen Arylation Reactions

X-Ray crystal structure of borane adduct of ligand 1. This adduct is stable to air, moisture and even column chromatography pro-R N H O ... O (S) ...
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Development of Enantioselective Nitrogen Arylation Reactions Russell D. Viirre Dept. of Chemistry and Biology, Ryerson University, Toronto, Ontario, Canada

O N pro-R H

O N H pro-S

3.3% Pd(OAc)2 6.6% ligand 1 1.4 eq. Cs2CO3 toluene, 100 °C

O H N

(R) (S) N O

Br

(R)-chiral center and (S)-chiral axis isolated as single diastereomer in 99% yield and 88% enantiomeric excess

achiral, with two enantiotopic amide groups

MeO PCy2

Ligand 1

X-Ray crystal structure of cyclized product, confirming configuration of chiral center and axis

X-Ray crystal structure of borane adduct of ligand 1. This adduct is stable to air, moisture and even column chromatography

ACS PRF #49493-UR1