Literature DB >> 15311947

Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

Yian Shi1.   

Abstract

Chiral ketones have been shown to be effective organocatalysts for asymmetric epoxidation of olefins with broad substrate scope. High enantioselectivity has been obtained for a wide variety of trans and trisubstituted olefins, as well as a number of cis olefins, with encouragingly high ee's for some terminal olefins. The stereochemical outcome of the reaction can be rationalized by a spiro transition state model.

Entities:  

Year:  2004        PMID： 15311947     DOI： 10.1021/ar030063x

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN： 0001-4842            Impact factor:   22.384


  52 in total

1.  New synthetic strategies for the stereocontrolled synthesis of substituted "skipped" diepoxides.

Authors:  Christopher J Morten; Timothy F Jamison
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

2.  Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols.

Authors:  Wei Zhang; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2007-01-17       Impact factor: 15.419

3.  Aspartate-catalyzed asymmetric epoxidation reactions.

Authors:  Gorka Peris; Charles E Jakobsche; Scott J Miller
Journal:  J Am Chem Soc       Date:  2007-06-26       Impact factor: 15.419

4.  Functional analysis of an aspartate-based epoxidation catalyst with amide-to-alkene peptidomimetic catalyst analogues.

Authors:  Charles E Jakobsche; Gorka Peris; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Vanadium-catalyzed enantioselective desymmetrization of meso secondary allylic alcohols and homoallylic alcohols.

Authors:  Zhi Li; Wei Zhang; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Syntheses and structural confirmations of members of a heterocycle-containing family of labdane diterpenoids.

Authors:  Daniel J Mack; Jon T Njardarson
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-17       Impact factor: 15.336

7.  Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis.

Authors:  Suresh Pindi; Jianbin Wu; Guigen Li
Journal:  J Org Chem       Date:  2013-03-26       Impact factor: 4.354

8.  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

9.  Asymmetric total synthesis of (-)-plicatic acid via a highly enantioselective and diastereoselective nucleophilic epoxidation of acyclic trisubstitued olefins.

Authors:  Bing-Feng Sun; Ran Hong; Yan-Biao Kang; Li Deng
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

10.  8,9-Isopropyl-idenedi-oxy-3-p-tolyl-1,6-dioxa-3-aza-spiro-[4.5]decane-2,10-dione.

Authors:  Chun-Sheng Ling; Qiang Wu; Shan-Shan Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-25
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