Document Detail


Synthetic Application and Structural Elucidation of Axially Chiral Dicarboxylic Acid: Asymmetric Mannich-type Reaction with Diazoacetate, (Diazomethyl)phosphonate and (Diazomethyl)sulfone.
MedLine Citation:
PMID:  21678947     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The last decade has witnessed the burgeoning research fields of chiral Brønsted acid catalysis. However, carboxylic acids, arguably the most general acids in organic chemistry, have rarely been used as chiral Brønsted acid catalysts. In this context, we developed axially chiral dicarboxylic acid, and evaluated its catalytic activity in asymmetric Mannich-type reaction of aromatic aldehyde N-Boc imines and t-butyl diazoacetate. To demonstrate the remarkable generality of this catalytic system, t-butyl diazoacetate was replaced to its phosphorous and sulfur analogs, (diazomethyl)phosphonate and (diazomethyl)sulfone, by which synthetically valuable chiral beta-amino phosphonates and beta-amino sulfones could be obtained with high enantioselectivities using identical reaction conditions. X-ray crystallographic analysis of axially chiral dicarboxylic acid complexed with a pyridine derivative revealed its unique internal hydrogen-bonding, a property which serves as a basis for its distinctive acidity and chiral scaffold.
Authors:
Takuya Hashimoto; Hidenori Kimura; Hiroki Nakatsu; Keiji Maruoka
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-6-16
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2011 Jun 
Date Detail:
Created Date:  2011-6-17     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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