Literature DB >> 16805540

Highly enantioselective CH oxidation of vic-Diols with Shi's oxazolidinone dioxiranes.

Kavitha Jakka1, Cong-Gui Zhao.   

Abstract

[reaction: see text] Through an analogical study of the transition states of CH oxidation and asymmetric epoxidation of terminal alkenes, the first dioxirane-mediated catalytic highly enantioselective CH oxidation method was realized with Shi's oxazolidinone ketone derivatives. Very good enantioselectivity (up to 92% ee) may be obtained for both asymmetrization of meso vic-diols and kinetic resolution of racemic vic-diols.

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Year:  2006        PMID： 16805540      PMCID： PMC2593872          DOI： 10.1021/ol060904a

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


  10 in total

1.  A Dramatic pH Effect Leads to a Catalytic Asymmetric Epoxidation.

Authors:  Zhi-Xian Wang; Yong Tu; Michael Frohn; Yian Shi
Journal:  J Org Chem       Date:  1997-04-18       Impact factor: 4.354

2.  Enantioselective epoxidation of terminal olefins by chiral dioxirane.

Authors:  H Tian; X She; J Xu; Y Shi
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

3.  Chemistry of dioxiranes. 4. Oxygen atom insertion into carbon-hydrogen bonds by dimethyldioxirane.

Authors:  R W Murray; R Jeyaraman; L Mohan
Journal:  J Am Chem Soc       Date:  1986-04-01       Impact factor: 15.419

4.  Isotope effects and the nature of enantioselectivity in the shi epoxidation. The importance of asynchronicity.

Authors:  Daniel A Singleton; Zhihong Wang
Journal:  J Am Chem Soc       Date:  2005-05-11       Impact factor: 15.419

5.  Transition state studies on the dioxirane-mediated asymmetric epoxidation via kinetic resolution and desymmetrization.

Authors:  Jon C Lorenz; Michael Frohn; Xiaoming Zhou; Jian-Rong Zhang; Yong Tang; Christopher Burke; Yian Shi
Journal:  J Org Chem       Date:  2005-04-15       Impact factor: 4.354

6.  Designing new chiral ketone catalysts. Asymmetric epoxidation of cis-olefins and terminal olefins.

Authors:  Hongqi Tian; Xuegong She; Hongwu Yu; Lianhe Shu; Yian Shi
Journal:  J Org Chem       Date:  2002-04-19       Impact factor: 4.354

7.  Relative reactivity of peracids versus dioxiranes (DMDO and TFDO) in the epoxidation of alkenes. A combined experimental and theoretical analysis.

Authors:  Robert D Bach; Olga Dmitrenko; Waldemar Adam; Simon Schambony
Journal:  J Am Chem Soc       Date:  2003-01-29       Impact factor: 15.419

8.  Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

Authors:  Yian Shi
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

9.  Novel pathways for oxygen insertion into unactivated C-H bonds by dioxiranes. Transition structures for stepwise routes via radical pairs and comparison with the concerted pathway.

Authors:  Mauro Freccero; Remo Gandolfi; Mirko Sarzi-Amadè; Augusto Rastelli
Journal:  J Org Chem       Date:  2003-02-07       Impact factor: 4.354

10.  Asymmetric epoxidation catalyzed by N-aryl-substituted oxazolidinone-containing ketones: further evidence for electronic effects.

Authors:  Lianhe Shu; Pingzhen Wang; Yonghong Gan; Yian Shi
Journal:  Org Lett       Date:  2003-02-06       Impact factor: 6.005
  10 in total
  1 in total

1.  Organocatalytic Highly Enantioselective Tandem Michael-Knoevenagel Reaction for the Synthesis of Substituted Thiochromanes.

Authors:  Rajasekhar Dodda; Tanmay Mandal; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2008-03-17       Impact factor: 2.415
  1 in total

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