Literature DB >> 12603106

Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives.

Martin J O'Donnell1, Jeremy T Cooper, Mary M Mader.   

Abstract

Optically active syn- or anti-beta-substituted-alpha-amino acid derivatives are prepared in 94 to >/=99% ee and 66-98% ds by reaction of the Schiff base acetate of glycine tert-butyl ester with chiral, nonracemic B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine (CdOH) or cinchonine (CnOH), base, and lithium chloride.

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Year:  2003        PMID： 12603106     DOI： 10.1021/ja0298794

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  7 in total

1.  Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

2.  Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates.

Authors:  Matteo Chierchia; Chunyin Law; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

3.  Unnatural Amino Acid Derivatives through Click Chemistry: Synthesis of Triazolylalanine Analogues.

Authors:  Pravin C Patil; Frederick A Luzzio
Journal:  Synlett       Date:  2017-07-24       Impact factor: 2.454

4.  Second-generation DBFOX ligands for the synthesis of beta-substituted alpha-amino acids via enantioselective radical conjugate additions.

Authors:  Biplab Banerjee; Steven G Capps; Junghoon Kang; Joshua W Robinson; Steven L Castle
Journal:  J Org Chem       Date:  2008-10-24       Impact factor: 4.354

5.  Stable Europium(III) Complexes with Short Linkers for Site-Specific Labeling of Biomolecules.

Authors:  Felix Faschinger; Martin Ertl; Mirjam Zimmermann; Andreas Horner; Markus Himmelsbach; Wolfgang Schöfberger; Günther Knör; Hermann J Gruber
Journal:  ChemistryOpen       Date:  2017-09-04       Impact factor: 2.911

6.  Distributed Drug Discovery, Part 2: global rehearsal of alkylating agents for the synthesis of resin-bound unnatural amino acids and virtual D(3) catalog construction.

Authors:  William L Scott; Jordi Alsina; Christopher O Audu; Evgenii Babaev; Linda Cook; Jeffery L Dage; Lawrence A Goodwin; Jacek G Martynow; Dariusz Matosiuk; Miriam Royo; Judith G Smith; Andrew T Strong; Kirk Wickizer; Eric M Woerly; Ziniu Zhou; Martin J O'Donnell
Journal:  J Comb Chem       Date:  2009 Jan-Feb

7.  Enantioselective carbene insertion into the N-H bond of benzophenone imine.

Authors:  Jian Yang; Peiran Ruan; Wei Yang; Xiaoming Feng; Xiaohua Liu
Journal:  Chem Sci       Date:  2019-09-18       Impact factor: 9.825
  7 in total

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