Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 32, Pages 11278-11287Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja104297g
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Funding
- NCRR NIH HHS [S10 RR013886-01] Funding Source: Medline
- NIGMS NIH HHS [R01 GM046059-19, R01 GM046059, GM-46059, R37 GM046059, GM-1S10RR13886-01] Funding Source: Medline
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We report efficient syntheses of axially chiral biaryl amides in yields ranging from 80-92%, and with enantioselectivity in the range 88-94% ee employing an asymmetric Suzuki-Miyaura process with Pd(OAc)2 and KenPhos as ligand. These studies demonstrate that electron-rich and electron-deficient o-halobenzamides can be efficiently coupled with 2-methyl-1-naphthylboronic acid and 2-ethoxy-1naphthylboronic acid. The yields and selectivities of the reactions are independent of the nature of halogen substituent on the benzamide coupling partner. Our investigations demonstrate that axially chiral heterocyclic and biphenyl compounds can also be synthesized with this methodology. We also report computational studies used to determine the origin of stereoselectivity during the selectivity-determining reductive elimination step of the related coupling of tolyl boronic acid with naphthylphosphonate bromide that was reported in a previous publication (J. Am. Chem. Soc. 2000, 122, 12051-12052). These studies indicate that the stereoselectivity arises from a combination of weak -(C)H0 interactions as well as steric interactions between the tolyl and naphthylphosphonate addends in the transition state for C-C coupling.
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