Literature DB >> 33326512

Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.

Ameya S Burde1, Shuklendu D Karyakarte, Eric D Sylvester, Sherry R Chemler.   

Abstract

Bridged bicyclic ketals display a range of bioactivities. Their catalytic enantioselective synthesis from acyclic 1,1-disubstituted alkene diols is disclosed. This reaction combines asymmetric catalysis with a distal radical migration. Alkynes and arenes undergo the group transfer.

Entities:  

Year:  2021        PMID： 33326512      PMCID： PMC8018521          DOI： 10.1039/d0cc06404a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  27 in total

1.  Observation and mechanistic study of facile C-O bond formation between a well-defined aryl-copper(III) complex and oxygen nucleophiles.

Authors:  Lauren M Huffman; Alicia Casitas; Marc Font; Mercè Canta; Miquel Costas; Xavi Ribas; Shannon S Stahl
Journal:  Chemistry       Date:  2011-09-12       Impact factor: 5.236

2.  Enantio- and Diastereoselective Spiroketalization Catalyzed by Chiral Iridium Complex.

Authors:  James Y Hamilton; Simon L Rössler; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2017-06-09       Impact factor: 15.419

3.  Synthesis of Spirocyclic Ethers by Enantioselective Copper-Catalyzed Carboetherification of Alkenols.

Authors:  Shuklendu D Karyakarte; Chanchamnan Um; Ilyas A Berhane; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-03       Impact factor: 15.336

4.  Photocatalyzed Metal-Free Alkylheteroarylation of Unactivated Olefins via Direct Acidic C(sp3)-H Bond Activation.

Authors:  Jie Fang; Wan-Li Dong; Guo-Qiang Xu; Peng-Fei Xu
Journal:  Org Lett       Date:  2019-05-31       Impact factor: 6.005

5.  Asymmetric Synthesis of Spiroketals with Aminothiourea Catalysts.

Authors:  Naoki Yoneda; Yukihiro Fukata; Keisuke Asano; Seijiro Matsubara
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-29       Impact factor: 15.336

6.  Enantioselective synthesis of spiroacetals: the conquest of a long-sought goal in asymmetric catalysis.

Authors:  Lara Cala; Francisco J Fañanás; Félix Rodríguez
Journal:  Org Biomol Chem       Date:  2014-08-07       Impact factor: 3.876

7.  Enantioselective copper-catalyzed carboetherification of unactivated alkenes.

Authors:  Michael T Bovino; Timothy W Liwosz; Nicole E Kendel; Yan Miller; Nina Tyminska; Eva Zurek; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-05       Impact factor: 15.336

8.  Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes.

Authors:  Fatima C Sequeira; Sherry R Chemler
Journal:  Org Lett       Date:  2012-08-15       Impact factor: 6.005

9.  Total synthesis of (-)-saliniketals A and B.

Authors:  Ian Paterson; Mina Razzak; Edward A Anderson
Journal:  Org Lett       Date:  2008-06-26       Impact factor: 6.005

10.  Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols.

Authors:  Dake Chen; Sherry R Chemler
Journal:  Org Lett       Date:  2018-10-11       Impact factor: 6.005
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