Literature DB >> 19319433

Highly stereoselective methylene transfers onto butanediacetal-protected chiral non-racemic sulfinyl imines using S-ylide technology.

David C Forbes1, Sampada V Bettigeri, Susanna C Pischek.   

Abstract

Diastereomeric ratios of >95 : 5 were obtained when performing methylene transfers onto imines originating from d-mannitol and (S)-(-)-2-methyl-2-propane sulfinamide or ascorbic acid and (R)-(-)-2-methyl-2-propane sulfinamide.

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Year:  2009        PMID： 19319433      PMCID： PMC2586643          DOI： 10.1039/b822779a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  12 in total

1.  Synthesis of a chiral aziridine derivative as a versatile intermediate for HIV protease inhibitors.

Authors:  B M Kim; S J Bae; S M So; H T Yoo; S K Chang; J H Lee; J Kang
Journal:  Org Lett       Date:  2001-07-26       Impact factor: 6.005

2.  Butane-2,3-diacetals of glyceraldehyde: a stable alternative to glyceraldehyde acetonide.

Authors:  Patrick Michel; Steven V Ley
Journal:  Angew Chem Int Ed Engl       Date:  2002-10-18       Impact factor: 15.336

Review 3.  Industrial syntheses of the central core molecules of HIV protease inhibitors.

Authors:  Kunisuke Izawa; Tomoyuki Onishi
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

4.  Aryl-substituted sulfonium betaines: preparation and use in the epoxidation of aldehydes.

Authors:  David C Forbes; Sejal R Amin; Christie J Bean; Michael C Standen
Journal:  J Org Chem       Date:  2006-10-13       Impact factor: 4.354

5.  Equilibrium Acidities and Homolytic Bond Dissociation Enthalpies of the Acidic C-H Bonds in As-Substituted Triphenylarsonium and Related Cations(1).

Authors:  Jin-Pei Cheng; Bo Liu; Yongyu Zhao; Xian-Man Zhang
Journal:  J Org Chem       Date:  1998-10-02       Impact factor: 4.354

6.  New approaches to the industrial synthesis of HIV protease inhibitors.

Authors:  Yutaka Honda; Satoshi Katayama; Mitsuhiko Kojima; Takayuki Suzuki; Naomi Kishibata; Kunisuke Izawa
Journal:  Org Biomol Chem       Date:  2004-06-23       Impact factor: 3.876

7.  Asymmetric synthesis of terminal N-tert-butylsulfinyl aziridines from organoceriums and an alpha-chloroimine.

Authors:  David M Hodgson; Johannes Kloesges; Brian Evans
Journal:  Org Lett       Date:  2008-06-04       Impact factor: 6.005

8.  Terminal aziridines by alpha-deprotonation/electrophile trapping of N-protected aziridine.

Authors:  David M Hodgson; Steven P Hughes; Amber L Thompson; Tom D Heightman
Journal:  Org Lett       Date:  2008-07-10       Impact factor: 6.005

9.  S-Methylidene Agents: Preparation of Chiral Non-Racemic Heterocycles.

Authors:  David C Forbes; Sampada V Bettigeri; Samit A Patrawala; Susanna C Pischek; Michael C Standen
Journal:  Tetrahedron       Date:  2009-01-03       Impact factor: 2.457

10.  One-carbon chain extension of esters to alpha-chloroketones: a safer route without diazomethane.

Authors:  Dengjin Wang; Mark D Schwinden; Lilian Radesca; Bharat Patel; David Kronenthal; Ming-Hsing Huang; William A Nugent
Journal:  J Org Chem       Date:  2004-03-05       Impact factor: 4.354
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  2 in total

1.  Relative Stabilities of Transition States Determine Diastereocontrol in Sulfur Ylide Additions onto Chiral N-Sulfinyl Imines.

Authors:  E Alan Salter; David C Forbes; Andrzej Wierzbicki
Journal:  Int J Quantum Chem       Date:  2012-01-01       Impact factor: 2.444

2.  (2S)-2-[(2S*,5R*,6R*)-5,6-Dimeth-oxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethyl-ethylsulfon-yl]aziridine.

Authors:  Toni Moragas Solà; William Lewis; Sampada V Bettigeri; Robert A Stockman; David C Forbes
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-27
  2 in total

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