Literature DB >> 11405747

Enantioselective epoxidation of terminal olefins by chiral dioxirane.

H Tian1, X She, J Xu, Y Shi.   

Abstract

[see reaction]. This paper describes an enantioselective epoxidation of terminal olefins using chiral ketone 3 as catalyst and Oxone as oxidant. Up to 85% ee has been obtained.

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Year:  2001        PMID： 11405747     DOI： 10.1021/ol010066e

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


  14 in total

Review 1.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

2.  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

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.  Quantitative DFT modeling of the enantiomeric excess for dioxirane-catalyzed epoxidations.

Authors:  Severin T Schneebeli; Michelle Lynn Hall; Ronald Breslow; Richard Friesner
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

10.  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
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