Catalytic Asymmetric Syntheses of α-Amino and α-Hydroxyl Acid Derivatives

Dubowchik, Gene M.

Catalytic Asymmetric Syntheses of α-Amino and α-Hydroxyl Acid Derivatives

Posted on 2009-05-15 - 00:00

Herein we report the first room temperature Heck reaction of aryl bromides and CH₂C(NHP)CO₂Me (P = Boc or CBz) to form ArCHC(NHP)CO₂Me, which are then used for the asymmetric syntheses of α-amino acids. We also report the first syntheses of ArCHC(OCOAr¹)CO₂Me (Ar¹ = Ph, 4-Cl−Ph) from ArBr and CH₂C(OCOAr¹)CO₂Me by the Heck reaction and subsequent successful asymmetric hydrogenation to afford α-hydroxyl esters in excellent chemical yields and good-to-excellent enantioselectivities.

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Han, Xiaojun; Jiang, Xiang-Jun; Civiello, Rita L.; Degnan, Andrew P.; Chaturvedula, Prasad V.; Macor, John E.; et al. (2016). Catalytic Asymmetric Syntheses of α-Amino and α-Hydroxyl Acid Derivatives. ACS Publications. Collection. https://doi.org/10.1021/jo900368k

https://doi.org/10.1021/jo900368k

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