Literature DB >> 18479136

Chiral phosphine-catalyzed enantioselective construction of gamma-butenolides through substitution of Morita-Baylis-Hillman acetates with 2-trimethylsilyloxy furan.

Ying-Qing Jiang1, Yong-Ling Shi, Min Shi.   

Abstract

Chiral multifunctional phosphine (R)-N-(2'-diphenylphosphanyl-[1,1']binaphthalenyl-2-yl)methanesulfonamide L2 or (R)-N-(2'-diphenylphosphanyl-[1,1']binaphthalenyl-2-yl)acetamide L3 is an efficient catalyst in the allylic substitutions of MBH acetates 1 with 2-trimethylsilyloxy furan 2 to provide gamma-butenolides 3 in good to excellent yields and enantiomeric excesses in the presence of water.

Entities:  

Year:  2008        PMID： 18479136     DOI： 10.1021/ja802422d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

Review 2.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

3.  Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.

Authors:  Alan M Hyde; Stephen L Buchwald
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

4.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2013-12-25       Impact factor: 6.222

5.  Iridium-catalyzed regioselective and enantioselective allylation of trimethylsiloxyfuran.

Authors:  Wenyong Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2012-09-11       Impact factor: 15.419

6.  Selective syntheses of Δ(α,β) and Δ(β,γ) butenolides from allylic cyclopropenecarboxylates via tandem ring expansion/[3,3]-sigmatropic rearrangements.

Authors:  Xiaocong Xie; Yi Li; Joseph M Fox
Journal:  Org Lett       Date:  2013-03-20       Impact factor: 6.005

7.  Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates with maleimides.

Authors:  Hong-Ping Deng; De Wang; Yin Wei; Min Shi
Journal:  Beilstein J Org Chem       Date:  2012-07-16       Impact factor: 2.883

8.  Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses.

Authors:  Yin-Wei Sun; Qin Xu; Min Shi
Journal:  Beilstein J Org Chem       Date:  2013-10-28       Impact factor: 2.883

9.  Asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with α-fluoro-β-keto esters.

Authors:  Lin Yan; Zhiqiang Han; Bo Zhu; Caiyun Yang; Choon-Hong Tan; Zhiyong Jiang
Journal:  Beilstein J Org Chem       Date:  2013-09-11       Impact factor: 2.883

10.  Chiral aminophosphines as catalysts for enantioselective double-Michael indoline syntheses.

Authors:  San N Khong; Ohyun Kwon
Journal:  Molecules       Date:  2012-05-11       Impact factor: 4.411
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