A facile synthesis of statine and analogs by reduction of .beta.-keto esters derived from Boc-protected amino acids. HPLC analyses of their enantiomeric purity

1988 ◽  
Vol 53 (4) ◽  
pp. 869-873 ◽  
Author(s):  
Juergen Maibaum ◽  
Daniel H. Rich
2012 ◽  
Vol 90 (5) ◽  
pp. 450-463 ◽  
Author(s):  
David I. Magee ◽  
Same Ratshonka ◽  
Jessica McConaghy ◽  
Maggie Hood

The synthesis of a large number of β- and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were few examples of complete Z selectivity, the use of tert-butyl acetoacetate with either aromatic or aliphatic aldehydes afforded Z selectivity. The selective reductions of these substituted keto esters was successfully achieved by using a combination of NaBH4 and CeCl3·7H2O or Yb(OTf)3, which allowed a facile synthesis of a large number of stereochemically pure substituted Morita–Baylis–Hillman adducts, including β,β-substituted adducts.


1993 ◽  
Vol 34 (46) ◽  
pp. 7409-7412 ◽  
Author(s):  
Pierre Chevallet ◽  
Patrick Garrouste ◽  
Barbara Malawska ◽  
Jean Martinez

ChemInform ◽  
2007 ◽  
Vol 38 (3) ◽  
Author(s):  
Zhenqiu Guo ◽  
Haoxi Huang ◽  
Qingquan Fu ◽  
Wenhao Hu
Keyword(s):  

Synlett ◽  
1996 ◽  
Vol 1996 (07) ◽  
pp. 665-666 ◽  
Author(s):  
Bernhard Westermann ◽  
Ina Gedrath

2017 ◽  
Vol 30 (5) ◽  
pp. 1704878 ◽  
Author(s):  
Simone A. Costa ◽  
Joseph R. Simon ◽  
Miriam Amiram ◽  
Lei Tang ◽  
Stefan Zauscher ◽  
...  

Sign in / Sign up

Export Citation Format

Share Document