Literature DB >> 22313246

Pd(II)/Brønsted acid catalyzed enantioselective allylic C-H activation for the synthesis of spirocyclic rings.

Zhuo Chai1, Trevor J Rainey.   

Abstract

A Pd(II)/Brønsted acid catalyzed migratory ring expansion for the synthesis of indene derivatives possessing a stereogenic spirocyclic carbon center was developed. This transformation is believed to mechanistically proceed via enantioselective allylic C-H activation with concomitant semipinacol ring expansion to the nascent π-allylpalladium species. Enantioselectivities as high as 98% ee were attainable.
© 2012 American Chemical Society

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Year:  2012        PMID： 22313246     DOI： 10.1021/ja2102407

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


  17 in total

1.  Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Authors:  Andrew J Neel; Jörg P Hehn; Pascal F Tripet; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

2.  Harnessing Noncovalent Interactions in Dual-Catalytic Enantioselective Heck-Matsuda Arylation.

Authors:  Yernaidu Reddi; Cheng-Che Tsai; Carolina M Avila; F Dean Toste; Raghavan B Sunoj
Journal:  J Am Chem Soc       Date:  2018-12-28       Impact factor: 15.419

3.  The progression of chiral anions from concepts to applications in asymmetric catalysis.

Authors:  Robert J Phipps; Gregory L Hamilton; F Dean Toste
Journal:  Nat Chem       Date:  2012-07-24       Impact factor: 24.427

4.  Enantioselective functionalization of allylic C-H bonds following a strategy of functionalization and diversification.

Authors:  Ankit Sharma; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-11-14       Impact factor: 15.419

5.  Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts.

Authors:  Carolina M Avila; Jigar S Patel; Yernaidu Reddi; Masato Saito; Hosea M Nelson; Hunter P Shunatona; Matthew S Sigman; Raghavan B Sunoj; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-18       Impact factor: 15.336

6.  Catalytic, Enantioselective α-Alkylation of Azlactones with Nonconjugated Alkenes by Directed Nucleopalladation.

Authors:  Sri Krishna Nimmagadda; Mingyu Liu; Malkanthi K Karunananda; De-Wei Gao; Omar Apolinar; Jason S Chen; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-27       Impact factor: 15.336

7.  Enantioselective Allylic C-H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis.

Authors:  Stephen E Ammann; Wei Liu; M Christina White
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-04       Impact factor: 15.336

Review 8.  Recent applications of chiral phosphoric acids in palladium catalysis.

Authors:  Van T Tran; Sri Krishna Nimmagadda; Mingyu Liu; Keary M Engle
Journal:  Org Biomol Chem       Date:  2020-01-07       Impact factor: 3.876

9.  Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes.

Authors:  Tuo Jiang; Teresa Bartholomeyzik; Javier Mazuela; Jochen Willersinn; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-24       Impact factor: 15.336

10.  Synthesis of Novel Spiro-Tetrahydroquinoline Derivatives and Evaluation of Their Pharmacological Effects on Wound Healing.

Authors:  Yan-Cheng Liou; Yan-An Lin; Ke Wang; Juan-Cheng Yang; Yeong-Jiunn Jang; Wenwei Lin; Yang-Chang Wu
Journal:  Int J Mol Sci       Date:  2021-06-10       Impact factor: 5.923
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