ChemInform Abstract: Amino Acids and Peptides. Part 70. Optically Active α-Amino Acids, N-Boc-Amino Aldehydes, and α-Amino-β-hydroxy Acids from 2,3-Epoxy Alcohols.

ChemInform ◽  
1989 ◽  
Vol 20 (37) ◽  
Author(s):  
U. SCHMIDT ◽  
M. RESPONDEK ◽  
A. LIEBERKNECHT ◽  
J. WERNER ◽  
P. FISCHER
ChemInform ◽  
2010 ◽  
Vol 33 (39) ◽  
pp. no-no
Author(s):  
Anders Boegevig ◽  
Karsten Juhl ◽  
Nagaswamy Kumaragurubaran ◽  
Wei Zhuang ◽  
Karl Anker Joergensen

Optically active α-amino acids can be converted into the corresponding doubly protected N,N-dibenzyl α-amino aldehydes. These react diastereoselectively with Grignard reagents, lithium enolates and Me 3 SiCN/ZnX 2 to provide the nonchelation-controlled adducts. Molecular modelling explains some of the results. The sense of stereoselectivity can be reversed if Lewis acidic chelating reagents are used. Undesired racemization does not occur.


2000 ◽  
Vol 65 (22) ◽  
pp. 7667-7675 ◽  
Author(s):  
Injae Shin ◽  
Mung-ryul Lee ◽  
Jiyong Lee ◽  
Mankil Jung ◽  
Weontae Lee ◽  
...  

1953 ◽  
Vol 18 (3) ◽  
pp. 297-302 ◽  
Author(s):  
K. BALENOVIC ◽  
N. BREGANT ◽  
D. CERAR ◽  
D. FLES ◽  
I. JAMBRESIC

2013 ◽  
Vol 135 (48) ◽  
pp. 18052-18055 ◽  
Author(s):  
Keith W. Bentley ◽  
Yea G. Nam ◽  
Jaslynn M. Murphy ◽  
Christian Wolf

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