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Literature DB >> 22135105

Catalytic enantioselective 1,2-diboration of 1,3-dienes: versatile reagents for stereoselective allylation.

Laura T Kliman¹, Scott N Mlynarski, Grace E Ferris, James P Morken.

Abstract

More with boron: The development of catalytic enantioselective 1,2-diboration of 1,3-dienes enables a new strategy for enantioselective carbonyl allylation reactions (see scheme). These reactions occur with outstanding levels of stereoselection and can be applied to both monosubstituted and 1,1-disubstituted dienes. The carbonyl allylation reactions provide enantiomerically enriched functionalized homoallylic alcohol products.

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Year: 2011 PMID： 22135105 PMCID： PMC3369812 DOI： 10.1002/anie.201105716

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

44 in total

1. Catalytic, enantioselective addition of substituted allylic trichlorosilanes using a rationally-designed 2,2'-bispyrrolidine-based bisphosphoramide.

Authors: S E Denmark; J Fu
Journal: J Am Chem Soc Date: 2001-09-26 Impact factor: 15.419

2. Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones.

Authors: Scott E Denmark; Jiping Fu
Journal: Chem Rev Date: 2003-08 Impact factor: 60.622

3. Nickel-catalyzed enantioselective three-component coupling of bis-1,3-dienes, aldehydes, and dimethylzinc.

Authors: Masanori Takimoto; Yuuki Kajima; Yoshihiro Sato; Miwako Mori
Journal: J Org Chem Date: 2005-10-14 Impact factor: 4.354

4. Concatenated catalytic asymmetric allene diboration/allylation/functionalization.

Authors: Angela R Woodward; Heather E Burks; Louis M Chan; James P Morken
Journal: Org Lett Date: 2005-11-24 Impact factor: 6.005

Review 5. Catalytic, enantioselective, vinylogous aldol reactions.

Authors: Scott E Denmark; John R Heemstra; Gregory L Beutner
Journal: Angew Chem Int Ed Engl Date: 2005-07-25 Impact factor: 15.336

6. Asymmetric construction of quaternary centers by enantioselective allylation: application to the synthesis of the serotonin antagonist LY426965.

Authors: Scott E Denmark; Jiping Fu
Journal: Org Lett Date: 2002-05-30 Impact factor: 6.005

7. Platinum-catalyzed tandem diboration/asymmetric allylboration: access to nonracemic functionalized 1,3-diols.

Authors: Jeremy B Morgan; James P Morken
Journal: Org Lett Date: 2003-07-10 Impact factor: 6.005

8. Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors: Christopher J Douglas; Larry E Overman
Journal: Proc Natl Acad Sci U S A Date: 2004-01-14 Impact factor: 11.205

9. Catalytic enantioselective allylboration of ketones.

Authors: Reiko Wada; Kounosuke Oisaki; Motomu Kanai; Masakatsu Shibasaki
Journal: J Am Chem Soc Date: 2004-07-28 Impact factor: 15.419

10. Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols.

Authors: Hugo Lachance; Xiaosong Lu; Michel Gravel; Dennis G Hall
Journal: J Am Chem Soc Date: 2003-08-27 Impact factor: 15.419

33 in total

1. Merging allylic carbon-hydrogen and selective carbon-carbon bond activation.

Authors: Ahmad Masarwa; Dorian Didier; Tamar Zabrodski; Marvin Schinkel; Lutz Ackermann; Ilan Marek
Journal: Nature Date: 2013-12-08 Impact factor: 49.962

2. Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling.

Authors: Gia L Hoang; Zhao-Di Yang; Sean M Smith; Rhitankar Pal; Judy L Miska; Damaris E Pérez; Libbie S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal: Org Lett Date: 2015-02-02 Impact factor: 6.005

3. Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates.

Authors: Qi Zhou; Harathi D Srinivas; Songnan Zhang; Mary P Watson
Journal: J Am Chem Soc Date: 2016-09-02 Impact factor: 15.419

4. Cationic Co(I)-Intermediates for Hydrofunctionalization Reactions: Regio- and Enantioselective Cobalt-Catalyzed 1,2-Hydroboration of 1,3-Dienes.

Authors: Krishnaja Duvvuri; Kendra R Dewese; Mahesh M Parsutkar; Stanley M Jing; Milauni M Mehta; Judith C Gallucci; T V RajanBabu
Journal: J Am Chem Soc Date: 2019-04-25 Impact factor: 15.419

5. Enantioselective synthesis of boron-substituted quaternary carbon stereogenic centers through NHC-catalyzed conjugate additions of (pinacolato)boron units to enones.

Authors: Suttipol Radomkit; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2014-02-24 Impact factor: 15.336

6. ω-Hydroxy isoprenoid bisphosphonates as linkable GGDPS inhibitors.

Authors: Nazmul H Bhuiyan; Michelle L Varney; Deep S Bhattacharya; William M Payne; Aaron M Mohs; Sarah A Holstein; David F Wiemer
Journal: Bioorg Med Chem Lett Date: 2019-08-20 Impact factor: 2.823

7. Catalyst Controlled Regiodivergent Arylboration of Dienes.

Authors: Stephen R Sardini; M Kevin Brown
Journal: J Am Chem Soc Date: 2017-07-12 Impact factor: 15.419

8. γ-Selective directed catalytic asymmetric hydroboration of 1,1-disubstituted alkenes.

Authors: Sean M Smith; Gia L Hoang; Rhitankar Pal; Mohammad O Bani Khaled; Liberty S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal: Chem Commun (Camb) Date: 2012-12-28 Impact factor: 6.222

9. Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors: Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal: Org Lett Date: 2020-11-18 Impact factor: 6.005

10. Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes.

Authors: John R Coombs; Fredrik Haeffner; Laura T Kliman; James P Morken
Journal: J Am Chem Soc Date: 2013-07-18 Impact factor: 15.419