Literature DB >> 17705500

Enhancing regiocontrol in carboaluminations of terminal alkynes. Application to the one-pot synthesis of coenzyme Q10.

Bruce H Lipshutz1, Tom Butler, Asher Lower, Jeff Servesko.   

Abstract

Two new "generations" of methodological advances are reported for the Negishi carboalumination of terminal alkynes. Use of simple, inexpensive additives that alter the Al-Zr complex formed between Me(3)Al and Cp(2)ZrCl(2) give rise to an especially effective reagent mix that results in virtually complete control of regiochemistry upon carboalumination of 1-alkynes. One timely application to coenzyme Q10 is highlighted. Regioisomers from subsequent coupling, which would otherwise be very difficult to separate, are avoided.

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Year:  2007        PMID: 17705500     DOI: 10.1021/ol701469e

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


  7 in total

1.  Synthesis and evaluation of novel analogues of ripostatins.

Authors:  Wufeng Tang; Shuang Liu; David Degen; Richard H Ebright; Evgeny V Prusov
Journal:  Chemistry       Date:  2014-08-11       Impact factor: 5.236

2.  Alpha-selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: practical syntheses of internal vinyl aluminums, halides, or boronates.

Authors:  Fang Gao; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

Review 3.  CoQ10 a super-vitamin: review on application and biosynthesis.

Authors:  Shraddha Shukla; Kashyap Kumar Dubey
Journal:  3 Biotech       Date:  2018-05-09       Impact factor: 2.406

4.  Total synthesis of piericidin A1. Application of a modified Negishi carboalumination-nickel-catalyzed cross-coupling.

Authors:  Bruce H Lipshutz; Benjamin Amorelli
Journal:  J Am Chem Soc       Date:  2009-02-04       Impact factor: 15.419

Review 5.  Catalytic enantioselective synthesis of chiral organic compounds of ultra-high purity of >99% ee.

Authors:  Ei-ichi Negishi; Shiqing Xu
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2015       Impact factor: 3.493

6.  Propargylation of CoQ0 through the Redox Chain Reaction.

Authors:  Robert Pawlowski; Maciej Stodulski; Jacek Mlynarski
Journal:  J Org Chem       Date:  2021-12-21       Impact factor: 4.354

7.  Preparation of Key Intermediates for the Syntheses of Coenzyme Q10 and Derivatives by Cross-Metathesis Reactions.

Authors:  Trang Nguyen; Hung Mac; Phong Pham
Journal:  Molecules       Date:  2020-01-21       Impact factor: 4.411

  7 in total

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