Literature DB >> 11950285

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

Hongqi Tian1, Xuegong She, Hongwu Yu, Lianhe Shu, Yian Shi.   

Abstract

This paper describes a new class of chiral oxazolidinone ketone catalyst for asymmetric epoxidation. High ee values have been obtained for a number of cyclic and acyclic cis-olefins. The epoxidation was stereospecific with no isomerization observed in the epoxidation of acyclic systems. Encouragingly high ee values have also been obtained for a number of terminal olefins. Mechanistic studies show that electronic interactions play an important role in stereodifferentiation.

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Year:  2002        PMID： 11950285     DOI： 10.1021/jo010838k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

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

Authors:  Kavitha Jakka; Cong-Gui Zhao
Journal:  Org Lett       Date:  2006-07-06       Impact factor: 6.005

Review 2.  Synthesis and Applications of Carbohydrate-Based Organocatalysts.

Authors:  Elżbieta Wojaczyńska; Franz Steppeler; Dominika Iwan; Marie-Christine Scherrmann; Alberto Marra
Journal:  Molecules       Date:  2021-11-30       Impact factor: 4.411

3.  Asymmetric epoxidation of 1,1-disubstituted terminal olefins by chiral dioxirane via a planar-like transition state.

Authors:  Bin Wang; O Andrea Wong; Mei-Xin Zhao; Yian Shi
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

4.  A diacetate ketone-catalyzed asymmetric epoxidation of olefins.

Authors:  Bin Wang; Xin-Yan Wu; O Andrea Wong; Brian Nettles; Mei-Xin Zhao; Dajun Chen; Yian Shi
Journal:  J Org Chem       Date:  2009-05-15       Impact factor: 4.354

5.  Synthesis of (R)-2-(benzyloxy)-tetrahydro-5,5-dimethylfuran by a new oxidative rearrangement.

Authors:  David Díez; Marta G Nuñez; Rosalina F Moro; Narciso M Garrido; Isidro S Marcos; Pilar Basabe; Julio G Urones
Journal:  Molecules       Date:  2006-12-18       Impact factor: 4.411

6.  Enantioselective epoxidation of nonconjugated cis-olefins by chiral dioxirane.

Authors:  Christopher P Burke; Yian Shi
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

7.  Highly enantioselective epoxidation of styrenes: implication of an electronic effect on the competition between spiro and planar transition states.

Authors:  Matthew Hickey; David Goeddel; Zackary Crane; Yian Shi
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-06       Impact factor: 11.205

8.  Asymmetric epoxidation of fluoroolefins by chiral dioxirane. Fluorine effect on enantioselectivity.

Authors:  O Andrea Wong; Yian Shi
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354

9.  Enantioselective linchpin catalysis by SOMO catalysis: an approach to the asymmetric alpha-chlorination of aldehydes and terminal epoxide formation.

Authors:  Muriel Amatore; Teresa D Beeson; Sean P Brown; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  1-Dibenzylamino-1-de-oxy-4,5-O-isopropyl-idene-β-d-fructopyran-ose.

Authors:  Shiyong Huo; Yueqing Li; Chaoyan Liang; Jihong Liu; Weijie Zhao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-15
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