Literature DB >> 20104883

Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates.

Hai-Lei Cui1, Ji-Rong Huang, Jie Lei, Zhao-Feng Wang, Shi Chen, Li Wu, Ying-Chun Chen.   

Abstract

The direct asymmetric allylic alkylation of beta,gamma-butenolides with MBH carbonates to access gamma,gamma-disubstituted butenolides containing adjacent quaternary and tertiary chiral centers has been presented in excellent stereoselectivities (86-96% ee, dr >95:5) and moderate to good yield (50-83%). Their synthetic utility has been well demonstrated by the facile construction of bicyclic lactones bearing 4-5 stereogenic centers.

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Year:  2010        PMID： 20104883     DOI： 10.1021/ol100014m

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


  4 in total

1.  Discrimination of Enantiomers of Dipeptide Derivatives with Two Chiral Centers by Tetraaza Macrocyclic Chiral Solvating Agents Using 1H NMR Spectroscopy.

Authors:  Lixia Fang; Caixia Lv; Guo Wang; Lei Feng; Pericles Stavropoulos; Guangpeng Gao; Lin Ai; Jiaxin Zhang
Journal:  Org Chem Front       Date:  2016-09-30       Impact factor: 5.281

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 Tripeptide Derivatives with Three Stereogenic Centers and Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents Derived from d-Phenylalanine and (1 S,2 S)-(+)-1,2-Diaminocyclohexane via 1H NMR Spectroscopy.

Authors:  Lei Feng; Guangpeng Gao; Hongmei Zhao; Li Zheng; Yu Wang; Pericles Stavropoulos; Lin Ai; Jiaxin Zhang
Journal:  J Org Chem       Date:  2018-10-30       Impact factor: 4.354

4.  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
  4 in total

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