Literature DB >> 17217268

Highly efficient synthesis of enantiomerically enriched 2-hydroxymethylaziridines by enzymatic desymmetrization.

Jun Young Choi1, Richard F Borch.   

Abstract

Both enantiomers of protected and unprotected 2-hydroxymethylaziridines are efficiently and enantiospecifically synthesized by using a combination of enzymatic and synthetic methods. PPL was used for lipase-catalyzed desymmetrization of N-protected serinol. [reaction: see text].

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Year:  2007        PMID： 17217268      PMCID： PMC2529399          DOI： 10.1021/ol062643a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Formation of Scalemic Aziridines via the Nucleophilic Opening of Aziridines.

Authors:  Stephen C. Bergmeier; Punit P. Seth
Journal:  J Org Chem       Date:  1997-04-18       Impact factor: 4.354

2.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors:  Paul Müller; Corinne Fruit
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  General catalytic synthesis of highly enantiomerically enriched terminal aziridines from racemic epoxides.

Authors:  Sang Kyun Kim; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

Review 4.  Enantioselective enzymatic desymmetrizations in organic synthesis.

Authors:  Eduardo García-Urdiales; Ignacio Alfonso; Vicente Gotor
Journal:  Chem Rev       Date:  2005-01       Impact factor: 60.622

5.  Enantioselective aziridination using copper complexes of biaryl Schiff bases.

Authors:  Kevin M Gillespie; Christopher J Sanders; Paul O'Shaughnessy; Ian Westmoreland; Christopher P Thickitt; Peter Scott
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

6.  Lipase-catalyzed resolution of (2R*,3S*)- and (2R*,3R*)-3-methyl-3-phenyl-2-aziridinemethanol at low temperatures and determination of the absolute configurations of the four stereoisomers.

Authors:  Takashi Sakai; Yu Liu; Hiroshi Ohta; Toshinobu Korenaga; Tadashi Ema
Journal:  J Org Chem       Date:  2005-02-18       Impact factor: 4.354

Review 7.  Aziridines: epoxides' ugly cousins?

Authors:  J B Sweeney
Journal:  Chem Soc Rev       Date:  2002-09       Impact factor: 54.564
  7 in total
  4 in total

1.  Synthesis of a phosphoserine mimetic prodrug with potent 14-3-3 protein inhibitory activity.

Authors:  Allison Arrendale; Keunho Kim; Jun Young Choi; Wei Li; Robert L Geahlen; Richard F Borch
Journal:  Chem Biol       Date:  2012-06-22

2.  Acyclic phosph(on)ate inhibitors of Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase.

Authors:  Keith Clinch; Douglas R Crump; Gary B Evans; Keith Z Hazleton; Jennifer M Mason; Vern L Schramm; Peter C Tyler
Journal:  Bioorg Med Chem       Date:  2013-03-05       Impact factor: 3.641

3.  Diversity-oriented synthesis based on the DPPP-catalyzed mixed double-Michael reactions of electron-deficient acetylenes and β-amino alcohols.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Molecules       Date:  2011-05-05       Impact factor: 4.411

4.  Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B2pin2: Experimental and Computational Studies.

Authors:  Lucilla Favero; Andrea Menichetti; Cosimo Boldrini; Lucrezia Margherita Comparini; Valeria Di Bussolo; Sebastiano Di Pietro; Mauro Pineschi
Journal:  Molecules       Date:  2021-12-06       Impact factor: 4.411
  4 in total

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