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

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

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...

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Veröffentlicht in:Journal of organic chemistry 2009-05, Vol.74 (10), p.3993-3996
Hauptverfasser: Han, Xiaojun, Jiang, Xiang-Jun, Civiello, Rita L, Degnan, Andrew P, Chaturvedula, Prasad V, Macor, John E, Dubowchik, Gene M
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Bromides - chemistry
Catalysis
Chemistry
Esters - chemical synthesis
Esters - chemistry
Exact sciences and technology
Hydroxides - chemistry
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Stereoisomerism
Substrate Specificity
Temperature
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900368k