Literature DB >> 21247085

Asymmetric synthesis of β-substituted γ-lactams via rhodium/diene-catalyzed 1,4-additions: application to the synthesis of (R)-baclofen and (R)-rolipram.

Cheng Shao1, Hong-Jie Yu, Nuo-Yi Wu, Ping Tian, Rui Wang, Chen-Guo Feng, Guo-Qiang Lin.   

Abstract

An efficient rhodium/diene-catalyzed asymmetric addition of arylboronic acids to α,β-unsaturated γ-lactams has been developed. The power of this methodology is further demonstrated by the concise synthesis of (R)-baclofen and (R)-rolipram.

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Year:  2011        PMID： 21247085     DOI： 10.1021/ol103054a

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


  8 in total

1.  Mild and rapid hydroxylation of aryl/heteroaryl boronic acids and boronate esters with N-oxides.

Authors:  Chen Zhu; Rui Wang; J R Falck
Journal:  Org Lett       Date:  2012-06-26       Impact factor: 6.005

Review 2.  Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives.

Authors:  Jianlin Han; Jorge Escorihuela; Santos Fustero; Aitor Landa; Vadim A Soloshonok; Alexander Sorochinsky
Journal:  Molecules       Date:  2022-06-13       Impact factor: 4.927

3.  Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium β-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to α,β-Unsaturated Carbonyl Compounds.

Authors:  Gary A Molander; Steven R Wisniewski; Mona Hosseini-Sarvari
Journal:  Adv Synth Catal       Date:  2013-10-11       Impact factor: 5.837

Review 4.  Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

Authors:  Katherine M Byrd
Journal:  Beilstein J Org Chem       Date:  2015-04-23       Impact factor: 2.883

5.  Direct β-selectivity of α,β-unsaturated γ-butyrolactam for asymmetric conjugate additions in an organocatalytic manner.

Authors:  Yuan Zhong; Sihua Hong; Zhengjun Cai; Shixiong Ma; Xianxing Jiang
Journal:  RSC Adv       Date:  2018-08-14       Impact factor: 4.036

6.  Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative.

Authors:  Tomoko Yajima; Eriko Yoshida; Masako Hamano
Journal:  Beilstein J Org Chem       Date:  2013-07-17       Impact factor: 2.883

7.  Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams.

Authors:  Dimitris Kalaitzakis; Manolis Sofiadis; Myron Triantafyllakis; Konstantinos Daskalakis; Georgios Vassilikogiannakis
Journal:  Org Lett       Date:  2018-02-08       Impact factor: 6.005

8.  Enantioselective Flow Synthesis of Rolipram Enabled by a Telescoped Asymmetric Conjugate Addition-Oxidative Aldehyde Esterification Sequence Using in Situ-Generated Persulfuric Acid as Oxidant.

Authors:  Bence S Nagy; Patricia Llanes; Miquel A Pericas; C Oliver Kappe; Sándor B Ötvös
Journal:  Org Lett       Date:  2022-01-20       Impact factor: 6.005
  8 in total

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