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

详细信息    查看全文

• 作者：Xiaojun Han ; Xiang-Jun Jiang ; Rita L. Civiello ; Andrew P. Degnan ; Prasad V. Chaturvedula ; John E. Macor ; Gene M. Dubowchik
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：May 15, 2009
• 年：2009
• 卷：74
• 期：10
• 页码：3993-3996
• 全文大小：171K
• 年卷期：v.74,no.10(May 15, 2009)
• ISSN：1520-6904

文摘

Herein we report the first room temperature Heck reaction of aryl bromides and CH₂C(NHP)CO₂Me (P = Boc or CBz) to form ArCHC(NHP)CO₂Me, which are then used for the asymmetric syntheses of α-amino acids. We also report the first syntheses of ArCHC(OCOArp>1p>)CO₂Me (Arp>1p> = Ph, 4-Cl−Ph) from ArBr and CH₂C(OCOArp>1p>)CO₂Me by the Heck reaction and subsequent successful asymmetric hydrogenation to afford α-hydroxyl esters in excellent chemical yields and good-to-excellent enantioselectivities.